This is no reason to not own property - I own a lot of properties (after all this is a real estate forum) - but I think it's important to understand how the system is set up and the current limitations imposed on the individual property owner.

As long as your municipality doesn't have additional restrictions (e.g.

As for short term rentals, most condo buildings will have restrictions/bylaws indicating that the minimum length of a rental is 30 days, 6 months or even 1 year and some buildings will even limit the number of units that can be rented at any given time.

And for almost the entire year it ran non stop up to Oct 25th when they added some restrictions and shut it off.

I know a little about the self directed IRA option but don’t like being restricted to retirement age for access.

I have considered renting a trailer instead (city does not restrict who I rent trailers from), but the extra effort would more than consume any savings.I suspect you are stuck with the one trash provider.  

Looking for advice on how to collect a large move-in sum and then monthly lease payment, considering each method has its limitations and restrictions.

Without emotion, send them a Pay or Quit notice when the rent is late and start the eviction filing proceedings that you can given COVID restrictions. 

I wanted to kick them out a while ago but were afraid of getting sued because of the COVID restrictions.

Any rental restrictions (long or short term)?