Re: Money problems
If you pick up everything (dig spots, chests) you have something like $11,000 in cash and sellable items coming into Bowerstone first time.
Coming into town, get all digs spots, cellars, chests in houses (daytime only when they are ususally open - no stealing) and go take all this stuff to Fairfax Gardens. Sell everything but your equipped weapons and clothes. (I don't add Knothole items to this as I keep those.)
In Bowerstone Old Town (if you gave Derek the warrants) you will get 50% off at stalls. Go to Weapons stall and buy everything you can afford. Go to Blacksmith in Market and buy til you run out of money. Sell in Fairfax. Leave FG and return immediately if you didn't spawn the correct traders first time.
Sometimes I get gems and better quality jewellery at Gifts trader in Old Town and resell in FG for easily double the money spent. I ususally buy the house (Helping Hand?) across from Gift/Food traders in Old Town to sleep when stalls close and repeat til rich. Buy the evil one at the foot of the stairs by Cemetary Rd if going evil.
I have had $2M gold before going to the spire without a delay to chop wood or forge the anvil. FYI Westcliff has fantastic weapons so make sure you got spendable gold before taking the quest with Hammer. I wait til just before going to the spire to buy all real estate available, jack up rents 50% and go spend ten years running to commandant.