A low maintenance condo rentable to good tenants sounds like a good starting point to me.I’m 56 and reasonably setup for retirement, so real estate is a stabilizing diversifier for me.

Curious how this will play out in the courts (granted it's LTR) and affect pricing products used for STR such as PriceLabs (which I use but have to seriously manually adjust for very specific reasons).

They're hiring PMs for a reason and they fire them for not maximizing cash flow.  

I wouldn't recommend it for a number of reasons. 

There's a reason that people try to buy properties off-market and that is because you can find sellers who care more about terms than maximizing returns.So start with a conversation: you already presumably have some rapport since it's your landlord and you've spoken before.

I have started 2 businesses to that end previously in my 20's; unfortunately neither of them worked out how I wanted for various reasons.

Quote from @Zeona McIntyre: Hey @Blake Winiecki I imagine you live in Florida but I would reconsider investing the area for one main reason - climate change.

There are 2 big reasons why I never had and would never have.1.

Most of the homes we built on these lots sold at a profit, but a couple did not, again, because of the reasons above. 

The only reason I chimed in is a lot of folks might take this as gospel for any and all areas.