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From the beginning of the Harry Potter series, the Weasley family's money problems come up repeatedly. Ron has to get all of his textbooks used, he is afraid to ask his parents to spend money on a new wand, and he doesn't even have enough spending money to buy a snack on the Hogwarts train. During the summer before Ron's third year, Mr. Weasley does win the Daily Prophet draw, but apparently he uses all, or nearly all, the money before the summer is out:

I couldn't believe it when Dad won the Daily Prophet draw. Seven hundred Galleons! Most of it's gone on this trip, but they're going to buy me a new wand for next year.

But when Ron returns to Hogwarts for his third year, he is able to spend money rather freely on his trips to Hogsmeade. With the prize money gone, how were Ron and his parents able to afford it?

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    Well, Ron dealt weed that summer. Rowling doesn't mention it because A. it isn't kid-friendly, and B. the only evidence of it is that he spends a little extra money in Hogsmeade, and she didn't figure something so minute was gonna bother anyone.
    – Misha R
    Commented Jul 20, 2015 at 5:41
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    They could have kept a small reserve as pocket money. I can't remember figures off the top of my head, but perhaps (as in the real world) "back-to-school" purchases are significantly more expensive than giving your thirteen year old a fiver at the occasional weekend, so it's not mentioned. Plus, Ron is thirteen. Remember how much stuff you were able to buy with a small amount of money at that age?
    – DavidS
    Commented Jul 20, 2015 at 9:02
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    Also, when else do the students get to spend money? Any money Ron gets or saves would be spent at weekends like this as on a day to day basis everything is provided for him at Hogwarts.
    – ThruGog
    Commented Jul 20, 2015 at 22:08
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    @MishaRosnach "Didn't figure something so minute was gonna bother anyone" - welcome to Stack Exchange. =)
    – corsiKa
    Commented Oct 13, 2015 at 16:15

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I'm going to go out on a limb and say that you've already answered your own question.

How much money does the family have in Book 3?

The 700 Galleons that Mr Weasley won is equivalent to approximately £3500 (about $5500). Even if they spent 90% of this windfall on their trip to Egypt, that would still leave the family with seventy Galleons.

Obviously seven of these galleons would be needed to buy Ron a new wand (since we know that all wands cost 7 Galleons) but that still leaves the family with 63 Galleons (£300) to spread out among the family over the following year.

How much does Ron actually spend in Hogsmeade?

First Trip
It's not clear. On his first trip, he and Hermione promise to buy Harry some sweets. They evidently had a Butterbeer and various free samples of fudge. On his return;

A shower of brilliantly coloured sweets fell into Harry’s lap.

But it's not clear whether he paid for any of this or, (far more likely) whether Harry gave him the money to buy him some sweets since he wasn't able to go himself.

Second Trip onwards
The same is true of pretty much every subsequent trip. Either Harry or Hermione are with him at all times. We don't see him spending his own money other than buying family presents or small one-off purchases like Butterbeer (two Sickles).

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