If I put all of my eggs in one basket (Florida in this case), paid off property and a hurricane blows everything away, FEMA is nowhere to be found and the insurance companies take years to pay what little claims they actually do pay, I suffer through it in a blown out house.

Right now the only utility at the garage is power so basically I am starting with a frame and a roof. 

And a condo can take longer to sell when you exit compared to a detached home.

The place I have is over 30 years old and a mansion ("mansion" in Japan means an apartment, not "mansion" like a huge house). 

These are professionals with additional training and a stricter code of ethics.

i also help with the set up, hosting and finding cleaners  I make it a one stop shop and the process makes it seamless and a sure thing with making money and keeping costs down.  

Buying rental properties is investing in a business and a place to make your money and time work for you.

Once you find someone willing to let you shadow them, approach it with professionalism and a willingness to learn.

Everyone thinks they can paint but there's a big difference between a professional paint job and a non-professional one (the latter usually actually damages the property instead of improving it). 

Id keep looking if it was not an approved short sale ( even an approved short sale takes a very very long time and theres no guarantee that you will even close on the house after months of waiting). q1)There are plenty of non traditional lenders that could offer you construction financing if the numbers make sense but it will cost you with points and a higher rate.