It is extremely odd the previous companies did not ask for that if they are collecting rent for you and issuing you disbursements.  

Then there’s city regulations—some places heavily restrict short-term rentals, so you’ve got to check the rules.If you find the right spot and automate stuff (guest communication, cleaning, etc.), it can be profitable.

They are very nice and can be helpful providing you what you can and cannot build on your property (Set back, height restrictions, front look etc).

There are also 'mezz' lenders (typically for larger transactions) who will cover up to 90% CLTV and require you to bring the remaining equity to the deal, and additionally there is Gap Funding in the form of unsecured personal debt.The latter can potentially be the most expensive option, but allows for true 100% financing as there are no restrictions for how to use these funds, as they are unsecured, and generally obtained through personal credit, income etc (since there is no collateral for obtaining these funds).

Most people don't sell an STR that is making them a ton of money so odds are it could look better, although they could be selling it for other reasons.

No, it is inside of an HOA neighborhood but the current regulations only restrict rentals under 30 days stays.

My thoughts are current housing supply + high rates + high home prices in OR are restricting our options and liquidating the brokerage to pay off the townhouse = $400k asset + $2,400 cash flow that we could then use to leverage or save into buying another property outright or scale into 4 plex and use the rent to pay down that mortgage too.

In-town properties are significantly easier to permit but also have some density restrictions.

That seems odd to me. 

This can provide a better depreciation benefit than traditional STR real estate.If permanently affixed to land, it qualifies for real estate depreciation (27.5 years for residential properties).Considerations:Zoning laws and campground restrictions may impact legality.Self-employment tax risk arises if you provide substantial guest services.Vacation home rules apply if personal use exceeds 14 days or 10% of rental days, limiting deductions.Audit risk is high, so keep detailed records of participation, expenses, and rental operations.Given the potential tax benefits and complexities, consulting a real estate tax professional is advised to ensure compliance and maximize deductions.This post does not create a CPA-Client relationship.