Does anyone have experience/recommendations of lenders who work with investors who have moved away from W2 income and can prove self sufficiency? 

Starter housing on the west coast is pretty tough unless the govmit buys the land and donates it.. land cost are huge part of it.. but in cities were you have lots that are basically worthless  as existing homes cost less than it cost to build.. those could be targets.

It is tough to find and usually takes some work, but that's the pocket of the market that makes the most sense to me. 

As a fellow Northerner, I tend to buy in the Southern half of the US for 2 reasons:1) you get much higher year-round occupancy rates in the South & it’s simply tough to earn a good ROI in the North if your place sits vacant for a big chunk of the year2) Culturally, the Southern half of the US seems to be a lot more accepting of STRs regulation-wise.

However, it's definitely been tough to find solid deals that cash flow well as of late, at least on the long-term side I find it to be true, and counting on potential increased demand is a tough investing strategy. 

Trusting lenders, agents, and contractors can be tough, but building a solid team and doing your due diligence will help ease that process.

@Andrew Freed is a good person to get in touch with about that as he is a MA multifamily investor who does a lot of meetups.STR is a tough way to start right now because in most markets the table stakes to be competitive are very high.

it's tough everywhere and it's really, really difficult for a new investor to do remotely especially when they really don't plan to go in person. 

the market is tough right now, with prices high, rates high, demand high, and inventory low. 

Trying to prove criminal is challenging whereas going after them in a civil case is much easier to prove and the way to get your money back.