These units are rare to pop up (I stay in one of the units each Summer) and usually are gone in a week....so I know the opportunity is 'there'.The goal is to relocate in 4-6 years and use this as a primary residence (but still travel and use as a vacation rental).I'm confident w/ the rental history of these units and comfortable with cash flow (hate having to initially throw down so much $$......but HI has their 'rules').

Maybe you ought to spend more of your time on raising money legally and forming Partnerships that keeps you in control and buying apartment complexes.He ideally looks for a 6 to 8 cap rate. 

Check with the city if this is a legal 2 unit building.

Owner would therefore face a large capital gains penalty upon selling the asset.Would it be possible/legal to execute a master lease option with a buyout that is intended to outlive the seller such that they can have fixed income for the remainder of their life, and such that their children can receive stepped basis by inheriting the asset that is already under contract (which was obviously written to be binding upon successor's and heirs).

I think Wenatchee would be a tough market for me to start in right now given the recent home price trend in the past few years, fewer tenants/less of a rental market, and the initial cost of a home.

Even a RUBS initiative won’t deliver 100% payment from residents and can spark a greater number to move out. 

You should be learning the legal way to raise money and forming Partnerships and buying apartment complexes under your control. 

Legally the operating LLC is acting as the owners agent by making decisions on leasing, maintenance, repairs, etc.

Does anyone have any good resources for an initial screening list of things to check for structurally or other issues a home inspector should find?

Whereas the general public doesn’t know a million real estate agents, tends to hire the first one they meet (when they’re ready) 70% of the time and tends to sign whatever “normal commission” you initially propose.The great thing about working with investors is you get access to wholesale priced contractors, you learn what questions to ask, and you learn how to analyze your own buy and holds or buy and sells.