Realistically you would expect the house to continue to appreciate during that time as well... even if at 3.33% appreciation - that is another $50,000 in appreciation you would make in the 3 years - give or take.  

At one point I was told I could obtain funding (non-conforming was the term that was used) with 12 months of bank statements.My question is what would make me more appealing to a lender; should I continue with 1099 work or go to W2??

We know they’re hard working and would like to continue working with them rather than move toward foreclosure, but we know they’re in over their heads if we continue under the current terms of the mortgage and don’t want to set them up for failure. 

I have no social sphere or contacts family or friends in Oregon (I don’t know anyone besides my fiancée).Goals: continue to have flexible schedule while enjoying what I do (selling real estate) and making good money.

I think over the foreseeable future we will see this continue due to rising prices in those markets like California and New York.

Continue to network with people in real estate, go to real estate meetups, connect with investors in the forums. 

Continue to expand my bareland funding for land flippers .

I am looking to connect with the investors there as the promotors are continuing to take Asset Management fees to the tune of $450K a year (on top of PM fees) even when their payout to the investors is around $20K a quarter (not meeting preferred) and the overall fund is negative about $450K.

My 2 cents is prices are crazy inflated right now, but believe it or not I think it will continue because of continued demand pressure for the area from people fleeing higher cost of living areas and moving there, with access to 87/17.

Explore Local Market Trends: Is Bend’s market likely to continue appreciating, or is it plateauing?