The HOA can decide to do a special project or make a short 3 story elevator more hurricane proof ($800000) or have issues after a hurricane and then you are definitely not ahead of the game.Please connect with me and I can maybe point you in a better direction.

I will use the 2 weeks off I have every month to researchI have owned a rental property in the past and it was extremely lucrative for me, and I didn’t even know what I was doing then haha! 

Then I’d use the cash flow to leverage future deals.

That's the only way you will know if it's legal.In a true wholesale deal you are putting the property under contract, then either assigning your contract or double closing. 

Assuming you purchased in your IRA for cash as most do, then there's nothing to deduct or depreciate because the income is non-taxable inside the IRA already.

I'm interested in flipping, and short-term rentals at the moment to build good cash flow, then pivot into more of a buy-and-hold/appreciation play 10-15 years from now.

If you get 100% of the purchase price covered then you should have sufficient funds for the closing costs based on what you're saying. 

Need to put the windows and doors in, and then start the mechanical rough inside.  

But then comes the bombshell..."

Lumber and plywood went up to the sky and then came back down but not down to previous levels everything else rose and stuck.