However, a common theme I hear when I ask them how they got into this business - they didn't know enough to be really risk averse. 

One theme that I noticed while reading this thread is that the words "never", "restricted", "limited",and "forever" come up often in arguments for leveraged real estate.   

And buy better quality real estate not just ITM trash assets.Do you notice the common theme-- it's buying real estate, how you get the capital is indifferent.

NO MONEY DOWN.There should be a bounty on these supposed "gurus".At least 4 books have been published and are being heavily promoted in the last year with the theme of purchasing an existing highly profitable business with no equity investment.  

If you want to enter that STR market you will need a lot of amenities and theme to keep up so furnishing costs could run 100k with modifications to support getting closer to the top in a tough market if it's not one that someone else was running.In terms of the cash, it gives you leverage on the buy, but I don't think you will like what you see on rates with a DSCR for STR if you only have 3-6 months of activity.

So I negotiated by finding out what dollar amount he needed from the me to sell?

One of my clients just converted his garage into a mini put put with a Star Wars theme..truly one of a kind.

It's listed in the events here for the first WED in May.

This of course is municipality specific but that's the general theme I observe.  

Im actually just finishing up on an ADU down the road at a different property so that may be a good indication if I can finish it quick enough to see resultsI also was thinking of making the barn a combination of both and make it like a bar themed loft for a guys / bachelor trip and build the simulator in with the living room as it can double as a projector type screen for netflix ect.