The long term plan would be to repeat this process until I build up enough capital that waiting 2 years between property purchases no longer makes sense and then transition to a new strategy.However, there are things about the Seattle area that concern me regarding the feasibility of this option.

@Dan Heuschele Totally understand your sentiment and for many people having 2 options between a 4 unit next to a 5 unit in the same neighborhood for the same price, purchasing the 4plex is a lot more feasible due to residential financing having not only fixed interest rate but usually a much less down payment requirement.  

While it would be so awesome to have a free place to stay when I go skiing in the winter, is it actually feasible? 

This is only really feasible if its a reasonably sized (300+ acres) all sports lake.

Then when you are ready to get for serious, have a proper pre approval done since you will usually need that for an offer.Once you know your approximate budget, you can determine if a buy and hold or flip in your area is even feasible. 

Maryville or Sevierville are both fairly feasible. 

Any experience with / idea about the feasibility of that?

Is there anyway to make a 97 loan feasible for an investment property?

Assuming all things were equal between Marin and Los Angeles except the purchase price, I would have to rent the car spaces for essentially double, which just isn NOT feasible.

. :-)The onus will come in my analysis regarding the feasibility of the deal.