I do understand the risk no matter what option I choose, I'm just trying to eliminate as much of the risk as I can in my later years.

We leverage all we can in the business side, but keep all its expenses & income settled there. 

Thanks Jay,We couldn't be where we are today without your help over the years.I want a fat dinner from you heheWe can bring the girls and let them chat while we talk biz :)Speak soon mate

That said, I have not yet sold a rental property so I have not experienced the high of getting a fat check at closing.

CheersElvis, if you’re looking to scale, I would focus on accessing the equity you can in order to jump to your next investment.

You may not make the same level of income you can in an STR but you're still looking at 2-2.5x market rent vs annual lease. 

Most of my op expenses on rentals run about 36% self-managed,  50% with a PM but I've had $30k outflow months so need a fat EF. 60% works for us but we live pretty modestly and don't have a mortgage. 

Again barriers to entry are steep but finding tenants and getting a nice fat rent check is very possible. 

My goal is to hopefully one day retire with that big fat nest egg, major equity and cashflow coming from all angles.

You can in Michigan.