Previous owner tore the tile off and put asphalt shingles on - which caused me to loose Historical designation.  

In the worst cases where you patch you need to break out the loose plaster and use wire mesh and replaster .

You can loose a fortune.

In a turnkey, are you bound to an agreement with the management company for a set period of years?

I know I'll loose the liability protection aspect of the LLC since the property will still be owned in my own name, but right now I'm more worried about doing things legally and in such a way that I'll pay the least taxes.Thanks for any advice

When you have a license you are bound to all the rules and regulations that go along with having that license and that includes disclosing the fact that you are a licensed agent.If you are planning to buy and sell land off market, you will just need to make sure that all parties are aware that you are a licensed agent but only acting on your own behalf and not representing any other interest but your own.

Once you get out of Attorney Review the 5th day; the remaining 10%-20% deposit is due but once you are out of Attorney review you are bound by the contract and the deposits are typically non-refundable unless due to one of the clauses (Inspections; Bad Title etc.).

Lots of loose ends.You should have done a mutual lease termination with 2 months rent as a lease buy out or termination fee and you would have been able to rent it or advertise available with basically offering a move in special of 2 months free to get a tenant ... 

This is easy to loose as a FSBO especially if you're inexperienced and don't know how to continue marketing efforts after a contract is accepted.  

Real estate is a roller coaster and sometimes you loose money.