laclongquan
Arcane
If you know what you are doing, heading to San Mona could bring you ~40 k (maybe more, I am not sure - shop quest, selling guns to Tony, prize in fights, mine, kingpin), some armours and Steyr (and 1 or 2 commando IIRC) which is great at start.
Drassen is nice to get because of airport, but you can grab just square with airport and buy whatever you want, defending it from much easier attacks.
Dressen couterstrike can be handled by cheesy way (not sure if they didn't fixed it) or you can retreat and attack at night. Hard but doable.
I went to San Mona on my way to Chinxena, I read somewhere that San Mona is supposed to be ''friendly'' toward you because it's run by the mob and there is no army there but I got attacked by some npcs in the streets, what's up with that? Anyway I'm in Chinxena now, gonna deal with this city first and take that mine.
Do your light fingers take what's not yours in an abandoned mine next door? That's kingpin's stash and a killing offense.