For example he has a six unit building in ca that has a tenant of 25 years in it that tenants son which was born in the unit which he is now 24 and has been renting a unit in the building for 5 years.

Hello Troy, Typically investment properties require 25-20% down payment.

Most if not all STR managers should have a number of actionable steps to increase revenue like the examples above.

While there is a chance, typically these need to be win-win situations for both parties

They are typically what investors use for rental properties once they are no longer eligible for conventional financing.

For example, I paid cash for houses and had to wait 6-months before I could put a mortgage on it.

For example, Fannie Mae loans if an existing first mortgage is being paid off through the transaction, it must be at least 12 months old at the time of refinance, as measured by the note date of the existing loan to the note date of the new loan.  

We as a firm have investors working with us who have small business and invest in rental properties all over the US for example big and small.Finding a real estate-focused tax professional and one who can help with advisory and grow with you would be my suggestion to focus your efforts on finding.

And while it does require this work on your end, the typical length of stay is in the 30-90 day range so you're only doing it a few times per year.

We all make the same claims. ie: “premium service”, “hand-picked homes”, homeowner-friendly onboarding”, “leading industry technology”, “24/7 communication or local support”, “maintenance programs”, “hotel quality linen program”, “preferred vendors” … blah blah blah I sell within what I would consider a “traditional” vacation rental market. ie - your vacation rental is likely not in danger of being put out of business by the local government… an example close to home for me - The City of Dallas’s recent STR Ban.