Financially, what’s the best way to use his services without wasting the first three (cheap) times?

I don’t intend to use the “Lottery” brownie feature for a reset – I’m not giving Evil Trout a cent, cuz’ I’m an bum like that. But now that I’ve hit level 7 and have “Threaten to Contact Authorities”, should I reset and omit “Think” and “Flirt” for better stats, or should I wait for level 10? I am starting to get into the tough forums, so another point or two in Frugality could make or break a raid.