I’ve had two sets of tenants that have both stayed 2 years with the current tenants probably planning to stay longer than that.

I've come up with a solid plan for the work and have a well-respected, but unlicensed welder to perform the work.

@Steve SmithLots of options with legacy planning I would recommend working with your advisors to create a detailed plan to make sure you are accomplishing your goals in the most effective way.  

Investing in short-term rentals in Florida sounds like a cool plan!

Plan on longer timeframes and overages.

That's ok so long as you have a solid plan for when you have a cap ex. 

We plan on using a money marketing account to save with until we buy our property to live in rather than it be a rental property after the next 6 years.

We plan to act as the GC for permit coordination, but mechanical, electrical, and plumbing contractors will file their permits individually under our GC status.

I think the biggest lesson learned (other than my failure to buy bitcoin instead) was to ensure I had a solid cash flow plan to implement the vision.

He should be on a commission split plan for his sales.