My 250K tax benefit will run out before his lease does on the 2 of 5 rule, so it might be a good time for me to sell - and help him with a lower rate than banks can give while giving me income until he refinances.

Have at least 2 exit strategies that you can use, if your plan doesn't work.For the cost of repairs, do not take responsibility for the unpermitted work, because purchasing the house will make it your responsibility and that's a risk that can undo your strategy in a heartbeat. 

Is the cost to repair their responsibility or ours?

My father was in the service too and planted his roots in South Florida as you are doing now when he transitioned out of military life.

Lease Options: This is better than a typical lease because there is an expectation that they will buy and in many cases, you can make the tenant responsible for some of the maintenance and also you get some option money.3.

It's crucial to conduct thorough due diligence, understand the local market dynamics, and be prepared for the responsibilities that come with being a landlord.

Important Tip for Wholesalers: 🌟Before diving into property contracts, it’s wise to check your local state and county regulations to see if you need a license to wholesale in your area.

The straightforward response is to 1031 into something bigger.

Such a detailed response!!

Property Management: Tips for managing your vacation rental remotely and ensuring a seamless guest experience.Pricing Strategies: Maximizing rental income while remaining competitive in the market.