I'm thinking you could do it if you were to lease the extra beds in your primary, plus your existing rental, plus a 600-700k luxury airbnb (10% down second home loan), plus an additional luxury airbnb purchased with conventional financing (20% down) and using the same operating systems as the first purchase.

Of course, if you think you're going to spend that extra money on "hookers and blow", as my friend @Jim K. would say, then you should probably leave it in the property. 

An extra $25-50 per month and you want to upgrade something in exchange. 

For example, is it an extra bedroom or bathroom? 

If you live in an extra unit you often can not have a stove or regular sink, but many people pull the stove for inspection and the put it back, but there may be an insurance issue there.

For example, I thought of drafting up a simple extra page to go along with a lease that has a new tenant waive their right to any future moratorium, like "I fully understand that if I don't pay the rent I can and will be evicted and waive my right any eviction moratoriums". 

It’s going to be an extra $270/mo, they didn’t blink.

Now decide is it worth selling for 20K extra?

If you're just looking for an extra $100/month, look to the Midwest.

. $10 for an extra pick up.