IG: @MattPriestJr Hey Willie, the best operators of rent by the room properties try to create a good atmosphere of likeminded people instead of random roommates that have nothing in common.

I did some research and it looks like the best way to go about it is via online platforms like Craigslist, SpareRoom, Roommates, and Facebook Marketplace.

Living with roommates is not early.

Not to mention all the phone calls and drama between roommates which hopefully will go well as Ive seen that work, especially if you screen. 

Also I am looking for an experienced realtor on Oahu that has worked with investors and understand the investor mindset.Type of house hacking strategies I am considering:Multiple units (duplex, multi family home)Single home with roommates (rent out extra bedrooms)Single home with vacation rental (Airbnb extra bedrooms)And here are my criteria:Budget 60-75k downpaymentEastern windward side of Oahu (Kailua and surrounding neighborhoods)Renter or vacation goer friendly locationLightweight rehab (no fixer)Aloha!

Adult roommates cohabitating on my block tend to live 2 per building and keep the third bedroom, which is small, as an office or guest room. 

I’m currently living here with a roommate and have a 3.3% interest rate loan on 300k and still owe about 280k.

He found a fixer upper and now has roommates.  

Would I be losing money and will there be headaches down the road with finding roommates and selling?

I'd rather you buy a place and have roommates rent out the extra bedrooms.