I've only operated 1 short term rental that I helped an owner convert to a midterm rental.

More travelers and RV owners are looking for private, unique camping experiences, and low-density parks with quality amenities are very appealing to this crowd.

.: There IS going to be a big impact on Real Estate, especially for Single Family and small Multi-Family that is Owner Occupied.The SALT Deductions are slated to expire at the end of 2025.Trump has already said that he will allow it to Expire:https://about.bgov.com/insights/elections/2025-tax-policy-cr...This is NOT a small change.The Standard Deduction gets reduced by about 40%.Then you get to deduct the SALT (State and Local Tax) that you paid PLUS up to $1 Million in Interest from your Mortgage against your Federal Tax Return.The only limiting factor will be AMT (Alternative Minimum Tax).In 2017 when this Cap was put into place, it made sense.However, now that the average Home sells for about Double what it was back in 2017, many normal Americans can benefit from the Expiration.I'm hoping that the Trump Administration does not extend the Cap.Too many people will love him more if he allows it to Expire!

Property owners get an annual update on their SEV & Taxable Values with their city property tax bill, typically sent in December.So now, the city assessor tracks the SEV, but homeowners are taxed based upon the capped Taxable Value.

Check with your local attorney/title company as many times you can void your owner's title policy with a quit claim deed.

You say investment but doing this long enough that is sometimes parlance for this deal might be looking like an investment but are you going to live there (owner occupied)?

You can use a Conventional owner occupied and as soon as you bring the equity to 20% through many invested or appreciation you can reappraise and drop the PMI.  

As a PM Co owner and broker specializing in STR Acquisitions I use AirDNA - but only the premium version. 

Specifically, here in Chicago, the Residential Landlord Tenant Ordinance (RLTO) explains that owners are not required to relocate tenants for cosmetic issues, unless the work significantly impacts habitability, as expressed above. 

(Owner passed.