This is assuming that Gandalf did not have a sixth sense about Bilbo having a much bigger role to play in the quest; and ignoring the fact that Hobbits are generally more difficult to be detected compared to other races.
To try and support this question, I recently read a post on another site concerning Hobbits and crime which briefly describes a policing force in The Shire who are known as The Shirriffs. Although not a lot of serious crime occurs in The Shire (this is ignoring Saruman and his merry band of Ruffians), there are still a few instances where there were theft:
- Vegetables being stolen from Farmer Maggot, particularly by our Merry and Pippin
- Sackville-Bagginses stealing silverware
Also, Bilbo is related to the Tooks who were not seen as being "good hobbits":
Tooks were mainly of Fallohide Hobbit stock, and were more adventurous than the other Hobbits. They also had quite a reputation for unusual behavior, a quality not exactly valued by most hobbits. For this reason they were seen as less respectable, and for the same reason they were one of the richer clans.
So it seems that our dear friend Bilbo has blood from both adventurers and criminals, which could also explain his wealth to some extent.
The question: Is there any evidence to suggest that Bilbo did have a criminal past, hence why he was given the title "Burglar"?