There's also growing regulation risk for the investor, thanks to the hospitality lobby convincing local Karens and pearl clutching city officials that short term rentals are nothing but drunk college kids and constant crime. 

Cleaner on my first property was constantly texting me with requests, schedule changes, personal issues/TMI, super long messages etc so moving over to Turno has been a nice respite. 

Consider attending local real estate meetups or joining online forums where local investors share insights and opportunities.Educate Yourself Continuously: The real estate market is constantly changing, so staying informed is key.

There's a few other things to think about too: 1 - Possible owner financing if he wants to still get a stream of income into retirement at an attractive rate compared to the rest of the market (win/win scenario, you don't need to come up with as much cash, and he makes a little $ on the %) 2 - Consider a post possession if he needs some time to move out but needs the cash up front for whatever reason 3 - Leave all the furniture/junk in the property and you'll handle clean up etc. 

Maybe about 13-15 acres with some harsh terrain, streams, dense woods I don't want to cut down ever.

It is also near a massive medical campus that is constantly growing in a decent size metropolitan area.

Upselling here is a thing of the past, the knowledge is constantly updated and new knowledge gets added at no extra charge because of the lifetime access of the program.

Once you choose your depreciation schedule, you cannot modify it mid stream, you are on that path until you either sell the property or deplete the depreciation life of that component. 

That made all the stress and anxiety worth it... the difficult tenants/roommates, constant noise, roommate drama, and lack of peace and privacy.This approach reflects the balance between comfort and profitability that Craig Curelop discusses in his book, The House Hacking Strategy.

I live there and invest and in my opinion the cities investment, constant development and growth are showing dividends for investors.