Things will likely go wrong, they won't work out exactly how the books and podcasts will have you believe, but you will learn so much just from that first deal.

I know a lot of good people that give it a shot and then walk away after a couple years because they can't handle dealing with bad renters or the market swings and things don't work out.

Always consider the possible exit strategies before you buy a property--I try to avoid buying properties that only have only one exit strategy or one use, because that's too much risk for me. ...If you found yourself in over your head with the management of the STR (which is much more time intensive to manage than a LTR), or if the STR market stalls and you have too much vacancy, you could pull the rip cord and turn it into a LTR (which would lower your cashflow, but would also free up a lot of your time, and lower your exposure to the numerous risks of STRs)...but if your STR only works as a STR, then you could easily find yourself between a rock and a hard place...know your exit strategies, and have sufficiently safe exit strategies to protect yourself from worst-case scenarios before you buy a property.Having said all that, the househack/STR strategies I described above would usually be significantly riskier, and significantly more challenging that just buying a normal house and house hacking it...Consider these two scenarios:1.

As well as being a lot more time intensive  if you do it yourself or costly if you have someone else do it.Originally posted by @Don Konipol:@Ken LatchersThanks Ken.

They ill be the "complainers" who won't work out anyway and you'll be evicting them sooner then non-complainers. 

Talk to him today and let him know you would like to buy his property and see what you can work out.

The idea of a partner is appealing but at the same time a hassle and am debating just hiring the work out and factoring it as a line item expense.

They tend to keep the space clean for the consumers and you usually have landlord friendly tenant laws.I have been down the multifamily route before and it is a more intensive asset to manage and a lot more BS with residential tenants and all of their excuses.I didn't like it but I do not like regular residential SFR either.

What might pen out on paper at 8.6% cash on cash will very likely work out a lot less in real life.

Overall it is a very difficult market to be in but depending on your investment strategy it can still work out in your favor.