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I'm entirely dissatisfied with the state of the existing answers, so here are the times someone using the 'reasonable person' test would consider Obi-Wan lying/stretching the truth while talking to Luke, in order of the most outright lie/misdirection to the smallest (spoiler alert: there aren't many):

1. When Obi-Wan said that Darth Vader betrayed and murdered Luke's father.

(Darth Vader is Luke's father, previously known as Anakin Skywalker)

2. When Obi-Wan said that Luke's father wanted Luke to have his old lightsaber.

(Anakin never referenced or discussed children of his own--real or desired--while talking to Obi-Wan, though it is likely true that, had Anakin maintained custody of his offspring, he would have helped them construct a lightsaber eventually)

3. When Obi-Wan mentions Luke's uncle Owen as the reason for Luke not receiving the lightsaber sooner and as a person who disagreed with Anakin's involvement in the Clone Wars.

(Owen probably didn't think Anakin should be involved in the clone wars but that's because Owen was a simple moisture farmer (in a family of moisture farmers) who thought everyone should mind their own business.

We don't know exactly what kind of words have been spoken between Obi-Wan Kenobi and Owen Lars since Obi-Wan arrived on Tatooine with baby Luke, so we can't ascertain whether Owen at some point during Luke's infancy/childhood said any of those things to Obi-Wan. Therefore this counts as a stretching of the truth or as misleading Luke, but not as an outright lie.)

4. When Obi-Wan mentions that Luke will need to learn the Force if he's to come with Obi-Wan to Alderaan.

(While this is true based on what Obi-Wan means (coming with him on his journey to defeat Darth Vader and the Emperor), it's a bit misleading because he doesn't mention any of these details. They're probably left out because they would discourage Luke, our reluctant hero, from leaving Tatooine. This is therefore misleading Luke at worst, and true at best)

All other lines Alec Guinness' Obi-Wan said to Luke are either true to the best of Obi-Wan's knowledge, matters of opinion, or otherwise not statements of testable veracity (commands, questions, et cetera).

I'm entirely dissatisfied with the state of the existing answers, so here are the times someone using the 'reasonable person' test would consider Obi-Wan lying/stretching the truth while talking to Luke, in order of the most outright lie/misdirection to the smallest (spoiler alert: there aren't many):

1. When Obi-Wan said that Darth Vader betrayed and murdered Luke's father.

(Darth Vader is Luke's father, previously known as Anakin Skywalker)

2. When Obi-Wan said that Luke's father wanted Luke to have his old lightsaber.

(Anakin never referenced or discussed children of his own--real or desired--while talking to Obi-Wan, though it is likely true that, had Anakin maintained custody of his offspring, he would have helped them construct a lightsaber eventually)

3. When Obi-Wan mentions Luke's uncle Owen as the reason for Luke not receiving the lightsaber sooner and as a person who disagreed with Anakin's involvement in the Clone Wars.

(Owen probably didn't think Anakin should be involved in the clone wars but that's because Owen was a simple moisture farmer (in a family of moisture farmers) who thought everyone should mind their own business.

In the movies, we never knew exactly what kind of words have been spoken between Obi-Wan Kenobi and Owen Lars since Obi-Wan arrived on Tatooine with baby Luke. However, we did see in the TV series Obi-Wan Kenobi that Owen wanted Kenobi to leave Luke alone and let him be raised ignorant of his past, repeatedly asking him to stop giving Luke toy spaceships and the like to play with and distract him from his chores around the farm. 

Therefore this counts as a stretching of the truth or as misleading Luke, but not as an outright lie.)

4. When Obi-Wan mentions that Luke will need to learn the Force if he's to come with Obi-Wan to Alderaan.

(While this is true based on what Obi-Wan means (coming with him on his journey to defeat Darth Vader and the Emperor), it's a bit misleading because he doesn't mention any of these details. They're probably left out because they would discourage Luke, our reluctant hero, from leaving Tatooine. This is therefore misleading Luke at worst, and true at best)

All other lines Alec Guinness' Obi-Wan said to Luke are either true to the best of Obi-Wan's knowledge, matters of opinion, or otherwise not statements of testable veracity (commands, questions, et cetera).

I'm entirely dissatisfied with the state of the existing answers, so here are the times someone using the 'reasonable person' test would consider Obi-Wan lying/stretching the truth while talking to Luke, in order of the most outright lie/misdirection to the smallest (spoiler alert: there aren't many):

1. When Obi-Wan said that Darth Vader betrayed and murdered Luke's father.

(Darth Vader is Luke's father, previously known as Anakin Skywalker)

2. When Obi-Wan said that Luke's father wanted Luke to have his old lightsaber.

(Anakin never referenced or discussed children of his own--real or desired--while talking to Obi-Wan, though it is likely true that, had Anakin maintained custody of his offspring, he would have helped them construct a lightsaber eventually)

3. When Obi-Wan mentions Luke's uncle Owen as the reason for Luke not receiving the lightsaber sooner and as a person who disagreed with Anakin's involvement in the Clone Wars.

(Owen probably didn't think Anakin should be involved in the clone wars but that's because Owen was a simple moisture farmer (in a family of moisture farmers) who thought everyone should mind their own business.

We don't know exactly what kind of words have been spoken between Obi-Wan Kenobi and Owen Lars since Obi-Wan arrived on Tatooine with baby Luke, so we can't ascertain whether Owen at some point during Luke's infancy/childhood said any of those things to Obi-Wan. Therefore this counts as a stretching of the truth or as misleading Luke, but not as an outright lie.

4. When Obi-Wan mentions that Luke will need to learn the Force if he's to come with Obi-Wan to Alderaan.

While this is true based on what Obi-Wan means (coming with him on his journey to defeat Darth Vader and the Emperor), it's a bit misleading because he doesn't mention any of these details. They're probably left out because they would discourage Luke, our reluctant hero, from leaving Tatooine. This is therefore misleading Luke at worst, and true at best.

All other lines Alec Guinness' Obi-Wan said to Luke are either true to the best of Obi-Wan's knowledge, matters of opinion, or otherwise not statements of testable veracity (commands, questions, et cetera).

I'm entirely dissatisfied with the state of the existing answers, so here are the times someone using the 'reasonable person' test would consider Obi-Wan lying/stretching the truth while talking to Luke, in order of the most outright lie/misdirection to the smallest (spoiler alert: there aren't many):

1. When Obi-Wan said that Darth Vader betrayed and murdered Luke's father.

(Darth Vader is Luke's father, previously known as Anakin Skywalker)

2. When Obi-Wan said that Luke's father wanted Luke to have his old lightsaber.

(Anakin never referenced or discussed children of his own--real or desired--while talking to Obi-Wan, though it is likely true that, had Anakin maintained custody of his offspring, he would have helped them construct a lightsaber eventually)

3. When Obi-Wan mentions Luke's uncle Owen as the reason for Luke not receiving the lightsaber sooner and as a person who disagreed with Anakin's involvement in the Clone Wars.

(Owen probably didn't think Anakin should be involved in the clone wars but that's because Owen was a simple moisture farmer (in a family of moisture farmers) who thought everyone should mind their own business.

We don't know exactly what kind of words have been spoken between Obi-Wan Kenobi and Owen Lars since Obi-Wan arrived on Tatooine with baby Luke, so we can't ascertain whether Owen at some point during Luke's infancy/childhood said any of those things to Obi-Wan. Therefore this counts as a stretching of the truth or as misleading Luke, but not as an outright lie.)

4. When Obi-Wan mentions that Luke will need to learn the Force if he's to come with Obi-Wan to Alderaan.

(While this is true based on what Obi-Wan means (coming with him on his journey to defeat Darth Vader and the Emperor), it's a bit misleading because he doesn't mention any of these details. They're probably left out because they would discourage Luke, our reluctant hero, from leaving Tatooine. This is therefore misleading Luke at worst, and true at best)

All other lines Alec Guinness' Obi-Wan said to Luke are either true to the best of Obi-Wan's knowledge, matters of opinion, or otherwise not statements of testable veracity (commands, questions, et cetera).

I'm entirely dissatisfied with the state of the existing answers, so here are the times someone using the 'reasonable person' test would consider Obi-Wan lying/stretching the truth while talking to Luke, in order of the most outright lie/misdirection to the smallest (spoiler alert: there aren't many):

1. When Obi-Wan said that Darth Vader betrayed and murdered Luke's father.

(Darth Vader is Luke's father, previously known as Anakin Skywalker)

2. When Obi-Wan said that Luke's father wanted Luke to have his old lightsaber.

(Anakin never referenced or discussed children of his own--real or desired--while talking to Obi-Wan, though it is likely true that, had Anakin maintained custody of his offspring, he would have helped them construct a lightsaber eventually)

3. When Obi-Wan mentions Luke's uncle Owen as the reason for Luke not receiving the lightsaber sooner and as a person who disagreed with Anakin's involvement in the Clone Wars.

(Owen probably didn't think Anakin should be involved in the clone wars but that's because Owen was a simple moisture farmer (in a family of moisture farmers) who thought everyone should mind their own business.

We don't know exactly what kind of words have been spoken between Obi-Wan Kenobi and Owen Lars since Obi-Wan arrived on Tatooine with baby Luke, so we can't ascertain whether Owen at some point during Luke's infancy/childhood said any of those things to Obi-Wan. Therefore this counts as a stretching of the truth or as misleading Luke, but not as an outright lie.

4. When Obi-Wan mentions that Luke will need to learn the Force if he's to come with Obi-Wan to Alderaan.

While this is true based on what Obi-Wan means (coming with him on his journey to defeat Darth Vader and the Emperor), it's a bit misleading because he doesn't mention any of these details. They're probably left out because they would discourage Luke, our reluctant hero, from leaving Tatooine. This is therefore misleading Luke at worst, and true at best.

All other lines Alec Guinness' Obi-Wan said to Luke are either true to the best of Obi-Wan's knowledge, matters of opinion, or otherwise not statements of testable veracity (commands, questions, et cetera).

I'm entirely dissatisfied with the state of the existing answers, so here are the times someone using the 'reasonable person' test would consider Obi-Wan lying/stretching the truth while talking to Luke, in order of the most outright lie/misdirection to the smallest (spoiler alert: there aren't many):

1. When Obi-Wan said that Darth Vader betrayed and murdered Luke's father.

(Darth Vader is Luke's father, previously known as Anakin Skywalker)

2. When Obi-Wan said that Luke's father wanted Luke to have his old lightsaber.

(Anakin never referenced or discussed children of his own--real or desired--while talking to Obi-Wan, though it is likely true that, had Anakin maintained custody of his offspring, he would have helped them construct a lightsaber eventually)

3. When Obi-Wan mentions Luke's uncle Owen as the reason for Luke not receiving the lightsaber sooner and as a person who disagreed with Anakin's involvement in the Clone Wars.

(Owen probably didn't think Anakin should be involved in the clone wars but that's because Owen was a simple moisture farmer (in a family of moisture farmers) who thought everyone should mind their own business.

We don't know exactly what kind of words have been spoken between Obi-Wan Kenobi and Owen Lars since Obi-Wan arrived on Tatooine with baby Luke, so we can't ascertain whether Owen at some point during Luke's infancy/childhood said any of those things to Obi-Wan. Therefore this counts as a stretching of the truth or as misleading Luke, but not as an outright lie.

4. When Obi-Wan mentions that Luke will need to learn the Force if he's to come with Obi-Wan to Alderaan.

While this is true based on what Obi-Wan means (coming with him on his journey to defeat Darth Vader and the Emperor), it's a bit misleading because he doesn't mention any of these details. They're probably left out because they would discourage Luke, our reluctant hero, from leaving Tatooine. This is therefore misleading Luke at worst, and true at best.

All other lines Alec Guinness' Obi-Wan said to Luke are either true to the best of Obi-Wan's knowledge, matters of opinion, or otherwise not statements of testable veracity (commands, questions, et cetera).