My heart is leaning OC given the family tie, obvious synergies with travel, etc. but my mind is leaning Tampa given the hard numbers. 

Right now inner city STR are struggling due to Covid and people not doing as much travel that is non vacation related.

My cleaners supply their own cleaning supplies at no extra cost (although you'll want to supply your own vacuum, bedbugs can travel from property to property in vacuums).

I am pretty confident it is not allowed but one can simply Google "deep dive cares act distribution my solo 401k" to watch the webinar.2) Yes re-contribution of CARES Act Distribution of Roth 401k to Roth IRA is allowed but one cannot re-contribute a CARES Act Distribution of a Roth IRA to a Roth 401k because the CARES Act does not create an exception to the Roth IRA rules that don't allow the rollover of Roth IRA funds to a Roth 401k.

At the same time, most guest booking longer stays, would prefer to have their pets travel with them so that’s also something to think about.

The limited interaction and desirable units have allowed me to keep tenants longer and allowed me to travel without any issues - for months at a time in this case.

Let me know if you want any more info about the process or who I used to set it up.I've used my retirement funds to secure and rehab 2 deals and it has given me invaluable experience, knowledge and confidence. 

@Mitchell BehmIf I could time travel and go back to a time when I was your age and in your position (am I seriously making myself sound like a grandpa!?)

The hardest is probably the first one since there are so many unknowns to me - and a lack of confidence.  

Painting ceilings is the worst type of painting in my opinion.It is the slowest because of the distance your roller has to travel from the ceiling to the tray on the floor each pass, you get paint drips not overspray dust on your face and your neck kills after about 30 minutes.