First, realize that I had the financial resources to protect myself in case of any disastrous moves and I've made some bad choices.

That does not make my choice right or wrong.

Volunteer work for a developer of your choice, my choice would be town houses development, spec building is not really inclined to whatever knowledge I got during school.

I know that I cannot do this alone, but that my success depends solely on my choice to be diligent, informed and to take action.

Roof - you didnt mention how much repairs are needed. most important, decisions about paint color, granite top, kitchen cabinets  tiles in bathroom, don't kill yourself in making those choices, be smart and quick, don't look at 100 designs to make a choice. 

You have the right to shop and pick the surveyor of your choice so if you think that is high that is on you to get another surveyor.  

That really becomes a personal choice for people, but stay with a frieze, if you do, unless you are using a professional designer.If you're in an area where "green" is important, think about using as many renewable products as possible, i.e. bamboo & cork for flooring, reclaimed wood as accents, etc.  

Their choice.

Buildium is looking like a smart choice. 

However, I think Jacksonville is probably another great choice here in Florida.