Essentially, Hart is a Smuggler with a debt to Hutt (@Nor'baal) However, with the War and such. How much does a man's background get into hindering his chances with the Republic.
I'm thinking more a Hondo Onaka role, he's a rascal that if you can reach him, he and his crew can be bought...
With something like that I think it has to do with what kind of offer/experiences he has with members of the republic. did he break republic law? is he willing to snitch on other criminals? that sort of stuff. if his bad deeds outweigh his good then he will have to deal with the consequences. Hondo also had a very specific series of events and relations with different characters that allowed him to illude punishment (relatively speaking)