Leader: I think Titus is the natural leader of the party, both by reputation (alignment) and background (noble), plus a tolerable charisma. That gets my vote, if [MENTION=6855204]tglassy[/MENTION] wants it.
Downtime: my problem with the downtime rules is the cost-of-entry for so many of the occupations. Currently Tommi has 36gp; that rules out Research, Training, or (best bet) gambling (it also bothers me that proficiency with cards/dice doesn't improve chances at Gambing; they've introduced a proficiency and then don't use it when it finally becomes mechanically relevant). Of realistic options, then, that leaves (in order) Pitfighting, Crime, Religion, or Work.
I can see Tommi working with another pit fighter, or possibly styling himself as a fixer, arranging fights and taking odds.Call it pit fighting, but on the understanding that it's not whatever official fights are happening, but after hours fights in the yard behind the pub, as he tries to provoke victors (or those defeated) who have started to drink to celebrate their wins or console themselves.