Any community with an HOA will most likely prohibit any short term rentals.  

The challenge I think you'll run into currently is the rates being prohibitive when it comes to the mortgage payment. 

My commercial loan prohibits owner occupancy

I did have a case where during a lease 2 roommates brought in a 3rd and I did not increase the rent, but do not think that is outright prohibited from discussion. 

We donated an easement only (not the land itself) on 1900 acres to prohibit logging or development for $4.5 million, which works out to about $2500 per acre. 

I absolutely collected first, last and security for my class-C rentals until NYS prohibited that practice back in 2019.Many tenants cannot manage their money properly, so this mitigates the issue of not being paid last month's rent when they need to move and the new landlord is receiving those funds they have allocated for their housing during the last month of their stay.This was also helpful to me to pre-screen who has their financial house in order and had saved for their moving costs as part of their planning.If I still could, I most definitely would - without exception.

This amount should be enough to provide a financial incentive for the tenant to leave but not so high that it becomes prohibitively expensive for you as the landlord.

this can achieve great return but capital Outlay is prohibitive for most (virtually everyone). 

Now, you can't do this with yourself, your business, and certain family members, due to the prohibited transaction rules governed by the tax code 4975. 2) Some individuals have large pre-tax 401ks that they rollover and then convert to the Roth IRA, paying the taxes now so they dont have to pay later out of the Roth. 

Schlough:Wis Stats 704.44(4m) prohibits a clause that: Requires payment by the tenant of attorney fees or costs incurred by the landlord in any legal action or dispute arising under the rental agreement.