I personally am a Military Mortgage BootCamp Instructor (I teach VA loans) and a real estate investor myself, so I have a very unique perspective on how to help people just like you. 

@Jacklyn Pascual, consider one other thing: Being a bit older gives you a unique perspective and you can leverage many years of life experience.

These properties come with their own unique set of challenges but for the right property can make a ton of sense.

Agree with mentions above, if you are starting your own PM "company" inside of another Broker's license - you are basically starting a division. 

Whatever the case we want a lot of exits, and we want to buy under market.As I said, turnkey doesnt fit our model, and we dont invest out of state (with one unique one off exception due to a child's college, and we are losing our shirt on that purchase).I think turnkey is fine if you do your own research, but I think its a mistake to consider turnkey a buy and forget investment.Maybe others who specialize on out of state purchases or turnkey investing could give you a little better guidance than I can.

I’ve got to side with @Sam Shin on this one, HI is a very unique market with an incredible amount of factors favoring homeowners.

I've been presuming one con for different locations is that you will need to build out a unique team for each location.

I'd recommend credit unions and smaller banks, they seem to be more willing to work with unique situations. 

When market is top cycle the sellers have lot's of more options out there with buyers and capital in the marketplace wanting to purchase.Of course the people selling course will tout they had great success etc. but will gloss over or fail to mention their examples were at  a unique time in the cycle and doing that same thing today will be very tough.

I have never offered this much more than asking, but I loved the character of the house and I place a premium on uniqueness in this market.