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)?

It will be one of the most restrictive and anti-landlord ordinances in the country if it passes. https://chicagorealtor.com/take-action-oppose-cook-countys-proposed-rtlo/

Covid made it harder because banks tightened lending for awhile earlier in the year.

The requirements will vary by city, but I would think SF would be the most restrictive.  

With the pandemic going on I know there are restrictions as far as evicting tenants, however since we'll be doing a month to month lease, do you foresee any issues asking them to vacate due to not renewing their lease?