I was going to do this later but here goes.....
A cosmetically challenged Milano with blown head gaskets being sold under duress is a parts car to everybody else. Not knowing anything, $500 tops. Is it an ABS car? If you are going to sell it for $500 and buy another daily with that money that you think you will be better off with, then keep the Milano and just go and buy your new to you $500 car. Then take forever to fix the Milano anyway. If you really have to change head gaskets, which won't be hard, would be time consuming, it's going to cost you more that $500 anyway, gasket set alone is $200.
Lots of good advise above. This is an old car, period, doesn't matter where it came from. It will need fixing, stop taking it to a mechanic for all this stuff. Buy some tools, at a $100 an hour for shop time, you can start getting quite a few tools. Even if you are working outside, in this instance you can still do a cooling system pressure test, retorque the head nuts. Change oil, take hoses off and on. If at the end of the day this is something you want to learn to do then great, tonnes of awesome help here to guide you. The flip side is, moving close to work and getting a bicycle...
Last thing, a Milano is generally in my mind a fairly robust car, I ran one for almost 10 years (98-06) as my daily driver in where most of you would consider the arctic, (Fort McMurray, Alberta) and it was one of the most reliable cars I've ever owned. Sure there was constant tinkering but it always ran. A Milano is worth putting effort into but it's going to hundred buck you to death until you get on the front side of the curve.
Enjoy the journey,