The area is great and near downtown and near a university so I think the potential for airbnb/short term rental is great for sporting events, downtown visits, alumni/parents visiting etc.Any fallbacks to having a tiny homes as an airbnb that I may not be seeing?

I even find myself reading the news or sports on my phone it becomes a nasty habit.. when I really should be reading a book LOL

Seems like an easy gamble I would take for sure. 

Negative cash flow is a gamble that appreciation will exceed your cash outflow.Hopefully your house appreciates while you are living in it. 

Or a gambling private lender.

Realistically, (If I understand correctly) sounds like he's got a lot more skin in the game and you are gambling a little because you don't have much experience. 

Doing them beforehand is a gamble.

With any chump change left over I’d go to a casino and do some sports betting or poker or table games but those fun investments aren’t really investments now are they. :)Or I’d go To the beach for two weeks and stay at a nice hotel.

If need local and sports, Playstation vue $50, on up to 6 TVs. $8 per set. 

But racing is a young man's sport and retired at the ripe old age of 25 yo at the end of 1979 season. 1980 I decided to sell real estate w only graduated HS.