Why not hire your realtor to do all that. 

I also think he needs another hobby like mission trips, sportscars, or fly fishing but that's my opinion. hahaYou could hire a maintenance/handy man in your market that understands real estate.

For you personally, does the potential hassle of dealing with a condo association outweigh the potential hassle of scheduling/hiring/managing contractors? 

I also hired a technician to inspect whole house to find any leakage.

When you buy a fixer-upper, renovate it, furnish it, and set it up as an STR, then manage it yourself, your return on investment will certainly be a lot higher than somebody who buys a turn-key property and hires a PM to run it.

Why not list it yourself and hire this person to manage it for you? 

This is not a passive business unless you hire a property manger.

When tenants can't pay the rent they can try to get a job, apply for welfare, apply for rent relief, go see the priest, or whatever.I run several businesses in California and I try to make believe that I am a manager who is working for a corporation in New York and I have to answer to that corporation for reasons e.g. why I made personal decisions to let tenants get away without paying their rent when I had the option to hire an attorney to evict the tenants.I own several fairly large apartment buildings and every tenant paid their rent on-time since COVID started with the exception of one 65-year old woman who lives in a studio and her rent is $1250.

We hired a property management company that did a better job of placing tenants than the previous owners had done.

Have you considered just keeping your duplex wherever it is and hiring a property manager to manage the day-to-day operation?