Stealth is helpful, yes. But when we're infiltrating we're not, like, sneaking in. We're pretending to be someone we're not in order to betray them.
Also really really think about the time expenditure. We have to spend another day farming money, there's travel time to consider, and then actually gaining information is going to take some time. Probably more than a day! Because, you know, if I was in charge of processing potentially deadly hires I wouldn't trust them faster than I can get certified to scuba dive.