Hey Andrew! Congrats on your orders to Alaska's emerald isle.
It sounds like you have a solid plan in place. My wife and I are trying to do the same thing. I'll be here in Kodiak until 2020. We bought a home in town that has a mother in law suite with its own entrance and we're renting it out on airbnb. There wasn't a lot to choose from when we were looking in 2016 and I feel we rushed into our purchase a bit but so far it's worked out pretty well. Since we've been here I've noticed that several duplexes have been sold.
If you are interested there is a 4 plex for sale just down the street from us. I've been trying to figure out how to get it for myself but the lender I'm working with has been a little discouraging saying that it'll be pretty difficult to justify moving from a single family to a 4 unit when working with the underwriter. I can email or PM the info on the property of you'd like.
I've only worked with Paula Laird (realtor) here. Her husband is a retired Coastie. You might cross paths with him since he works on base. But Paula is investor friendly. In fact, she has been encouraging me to get an investors group going and even offered her office as a place to hold meetings.
As far as contractors and stuff like that I can only recommend a good plumber and an electrician since those are the only ones I've worked with here so far. I can PM you their info as well.
