Had horrible luck making good money without too much time and labor involved. 

I also wouldn't be involved in day-to-day operations onsite.

The property manager will be involved for years, and they want it to be something easy to manage.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

If you want to scale, it likely won't involve you running your own renovations as a GC.

Ensure that the savings from the new loan outweigh the costs of the prepayment penalty and any closing costs involved in the refinance.6.

I assume there’s no realtor involved or they’d be upside down.

And treat this as 1/5th space as a rental.Or down the road, would it be better to have the entire property (home & garage/room) rented out to everyone involved and the property become an investment property. 

Because first and foremost it requires you getting INVOLVED, putting in some rep's, and if you won't get involved and won't put in the rep's you will never, I repeat you will NEVER succeed in investment real estate or any business venture EVER, full-stop. 

I won't ever close on another OOS property without walking it first but that involves paying for lots of flights and hotel/rental car costs if flying out there to make an offers but the $1500 to $3000 would be worth the cost to me to save on future headaches.