Concerning the random quests, the mod already has something to remedy the situation.
The solution is to reset the quests on offer through the barkeepers shop menu. Then give him his tip, and if the there's no mission in town repeat the procedure. I've taken all cities with random quests to +100 relation without any negative side effects on the game.
The only thing I noticed is that on a few repeated fed-ex quests the journal entries don't work right and stay on in the journal, but the quests still work.
Progress is quite quick because all the traders are eager to hand out the 'hoodlums' mission once (and mayors the 'fugitive gang'), which give a good boost to standings and enable most other quests for the town in question.
A possible solution to do this more comfortably could be to edit the quest files so that with low standings these missions would be given higher preference. Or maybe the barkeep (for an extra tip) could always generate a quest for his own town... Certainly better than trying to give a high-level quest and getting the 'you don't look the part' reply