Who thought we would have a pandemic and governors would restrict evictions.  

I'd like to start something as soon as COVID restrictions allow.

I know it’s possible, but seems like it could be complicated and I keep running into roadblocks/restrictions.

Key things to consider will be restrictions in the area you want to buy, financing (make sure you're lender will allow STR income to be counted), and if you will self manage and coordinate cleanings or hire a company to do that. 

Then restrictions are much less than with a bank.

You could probably do it in a more rural setting where there are less restrictions, but most renters don’t want rural

Our geographical barriers to growth combined with designated open space restricts supply, causing prices to go up, up, up.

The record increase in coronavirus cases has put more strain on the U.S. economic recovery, with many cities and states reimposing restrictions and some businesses being forced to sideline workers again.

I have a tenant that broke his lease back in March but Covid restricted me from being able to evict.

You may want to check deed restrictions (DRs) in your section of the subdivision to make sure they allow 2 units.