I’ve seen counties “grand fathering” STR owners for a set amount of time.

What are the fixed and variable costs associated with having a short-term rental vs long-term rental?

For starters, is the property you are selling a property you have held for investment (not a fix and flip where you are a dealer)?  

They are substantially changing other terms in the lease by asking for an additional option to renew, asking us to refund the security deposit, asking us to allow assignment without our consent, and insisting on us paying a commission amounting to almost $10K for the privilege of giving up all that.I just wanted a sanity check that this should not be all that difficult or onerous on us!

More often that not, the PHA section 8 voucher can get you rents that exceed the typical market rental amount in the area.

You'd be surprised to learn that sometimes you will need to fix something; you'll need enough time to do so.

I have been working on rental applications where the county issued some fixes last year.

Dad is more interested in fix and flip but open to other methods as well. 

I would have to agree with all of the people that have replied to your post, and I think you may be  referring to other people's money" There is a reason that they are called private lenders, their qualification approval guidelines are based mostly on the amount of money one puts down.

Outside of hard/private money you might have a tough time financing these due to the low values/loan amounts, especially the second one.