I did, well as they say no good deed goes unpunished, she ripped me off for 10k.

I am currently under contract for a very unique off market property that is waterfront (Manatee river, Bradenton, FL) and very close to the seawall(1958) & rip rap(2016).

I rehabbed with paint, new flooring, new fixtures and staging.

As for vacation spots, easiest way to increase attraction is getting creative with designs, especially with paint and get GOOD photos with professional cameras.

And if there's any paint chipping it's likely you fail automatically so cover those up.

She then patched every hole herself and painted over the patches in the wrong color paint.

What's my best bet, painting over it or going over it with vinyl siding.

I can't speak for contractors, but as a DIYer, I know even the most basic kitchen renovation may end up costing me 10k if I were to do it myself. 2-3k for cabinets. 1k for plumbing and fixtures1k for electrical and fixtures2-3k for granite countertops1k for tiling/flooring1k for miscellaneous like painting, etc. 

Installed a new roof and fresh paint.

It's a basement rip it out, wash it all down, move on.