Biggest thing is to make sure the agent and title company are competent in Seller Financing, I personally close my Seller Financing deals with a title company who has a real estate attorney on staff.   

@Nathan FrostSell your worst 2 or 3 properties that you expect will be the biggest headaches and the ones you can live without.

Even with hurricane Ian (biggest in history for the area) nothing over there would of flooded.

This would cover your biggest risk, which is liability lawsuit if someone is injured on the trampoline.Regarding the shed, was it installed in compliance with all local municipality statutes?

You need to get rid of your biggest Liability first!!

My biggest concern is being late to start as I am 50!!!

We have been blessed to serve a a ton of Bigger Pockets clients and the biggest challenge we have with house hackers is the FHA Self Sustainability test.. 75% of the overall rent has to cover the PITI.. with rates where they are this has been a big challenge. 

Note this is the biggest issue, but other things to consider is no revenue until ADU is built and rented.  

.: Quote from @Joe Fish:Long-term fixed rate debt and quality location are arguably going to be the biggest two biggest hedges against the play against infrastructure and land.  

I've never had a tax sale turn out to be void, but it is my biggest fear with Alabama tax sale investing.