Even the contractor would be foolish to cover it (insurance or not) without evidence that the car had paint no it.

It is imperitive to budget for the phantom expenses such as capex, repair, maintanence, and property management (even if you are self managing).

Even if I get her to sign, I really doubt she has kept records of my specific transactions, and my gut tells me she would lie if the state called her up and asked her. 

If so, will it spook future buyers even if the foundation has been taken care of?  

Ideally, you could find something liquid (money market) or fixed for a duration until you need it (CD, etc) with a rate approximating inflation but rates (even with talk of some incremental raises coming) still won't yield much.I think you have a good point about return.

I have tried to mitigate the problem for weeks now and have even addressed it with the HOA and Board of Directors because it’s a building problem that is invading my unit now.  

You will need to show gross negligence to even think about sending him a demand letter.

Im torn between multifamily and single family in jupiter but I feel single family would be easier but not as much cash flow.

Personally, I started out as a bird dog and wholesaler finding deals for other investors in single-family homes.

I have even deeply discounted some week days this fall to see if I can get an Airbnb booking.