This where I'm probably leading more with my heart than with my head, but I want to buy a place in Bend that will at least break even for me.

My biggest advice for out of state investors is finding the right team members who has your best interest at heart (and not chasing a commission check or see you as a paycheck!).

It is very important to find an agent that you vibe with and that has your best interests at heart. 

I sold the portfolio earlier this year for a good ROI and want to look into Orlando, where my heart is as a Disney nut.Goal is to build or buy a long term unit or two that will, at the least, pay for themselves, maintenance, taxes, and a pm… with a touch of profit at the end of each month.  

Plant City, Winter Haven, Davenport, Brandon..... many good buys near main roads, but outside of the heart of the cities.

I would do this in a heart beat if I can get conventional financing.

Up the coast on the west side, near Waianae, as well as up the East coast past Kaneohe but before Turtle Bay, and finally in Kalihi valley before hitting the heart of Honolulu, there are some very affordable pockets, but perhaps for good reason. 

So, yes, thinking about all the interest you could possibly pay over 30 years can be heart-stopping... and it should be.

My biggest advice for out of state investors is finding the right team members who has your best interest at heart (and not chasing a commission check or see you as a paycheck!).

Your heart is set on investing in a market that is NOT good for investing in.