A coach makes sense if you are 23 and want to increase your skills enough to earn a living with the sport.

Despite the storms in W FL we are seeing YoY rate and occupancy increases 24-25.  

The 401k is a valuable asset but its my thought that I can use this asset to further increase my portfolio by putting that money to better use.

Also, watch out for any litigation or construction issues that could lead to HOA fee increases down the road.Alternatively, you could consider a good deal on a single-family home or a 2-4 unit property.

Has another title company been engaged?

There are a lot of ways to crash and burn, so increasing the odds of succeeding long term should be your highest priority. you can always sell your local assets once you're comfortable managing rentals and ready for a market that better-suits your criteria. btw, kudos for being self-aware of your limitations.

*As a side note, I think maybe it would be fun also to try and identify where new technology or machine-learning driven approaches could increase efficiency in the spaceAs for my financial situation, personally, I have around 50k saved but 20k of it is tied up in assets I don't want to pay capital gains tax on.

Our last deal we engaged a mortgage broker that also brought a Private Equity LP (Limited Partner) to the deal. 

the key to a BRRRR, whether it's going to be an STR or LTR, is this:distress.you need to find a significantly distressed property, such that you can increase the ARV via the rehab. 

I own 4 two/three flats bought between 2013 and 2020 in Forest Park, Illinois, at low interest rates and prices in 200000's  They cash flow nicely and prices have increased a lot.