Look, we were for most part playing a game of American Football for a long time.

This in turn will kill your exit strategy if you are not doing your due diligence and playing conservative.

Playing around with my Excel spreadsheet and got to thinking about selling my rental property in the next few months vs waiting until it's paid off in Jun 2027. 

That will also play into it.

Contractors play such a huge role in real estate projects.

So seems like a decent play for cash flow but not much for appreciation.

Retirement accounts are designed to be invested passively so when the IRS sees you running an active business in it, to level the playing field between retirement accounts and other business the retirement account incurs UBIT. 

.: I always play it by ear.

Lost in all of this has been the significant role technology now plays in listing and selling real estate.

I would say you need to play to your strengths, whatever those might be.