So, things change a bit.If it is his personal home, there are more restrictions.For an investment property, if you take over his financing, read through the deed of trust (mortgage) and see how they handle transfer of ownership.

Just my personal opinion - get a mentor or a person who already has good experience running STR business, preferably in your area (but not 100% required). 

@Lauren MerendinoI strongly believe that your chosen market should be somewhere that you can go to in person / have strong personal knowledge of / have family or a network in already.  

You must report rental income on Schedule E and can deduct rental expenses like repairs, maintenance, property taxes, mortgage interest (allocated between personal and rental use), and depreciation for the rented portion.

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

It should be from someone who uses that person.

So the question becomes based on their individual and personal tax situation what is the estimated tax burden they'd save? 

I have known and worked with Matt for years.I have attended his training and hired him as a consultant.He is hands down the best at what he does.I have personally raised over $50 million for my hard money lending company.I am grateful for a lot of people who helping me with this success and Matt is at or near the top of that list.

Whether the seller was open to a buyer commission or not, I wouldn't put an additional cost into any personal purchase.  

It also gives you multiple work surfaces so you can have more than one person in the kitchen without getting in each others' way.