For me it boils down to more of a personal decision - can I afford two homes, do I want to have two homes and the stress of it, or just take my money out of one and put it in another.

Strengthen Your ProposalDevelop a Business Plan: Include:Vision: Your goal of creating a micro-home community.Market Research: Show demand for affordable or small-footprint living in your area.Financial Projections: Break down costs, ARV, and anticipated ROI.Experience: Highlight your previous fix-and-flip and demonstrate your learning curve.Present a Solid Development Plan:What is the size and scope of the project?

My ultimate goal is not using my savings during this process, because I want to train myself from the onset to think creatively and not deplete my reserves instead of finding a better deal or more productive relationship.

Lower property taxes, affordable housing compared to LA (CA buyers are usually cash buyers because what they net from their smaller home in CA can get them a bigger home here, often covered by what they net from their CA sale), allergies (smog), and politics. 

why not build in a more affordable price point. the largest two builders in America build non luxury maybe take their advice?

I am wondering if anyone has good places to research affordable yet healthy/upcoming markets to invest in MA. looking to get into my first househack/203k so just trying to figure out where to look.

Your VA loan will be crucial to your real estate investing growth, especially since it affords you the potential opportunity to own more than one property, depending on your overall allotment.For active military personnel, that conundrum of where to invest and where you will end up is always part of the issue that sometimes causes analysis paralysis so it's great you have one in VA Beach already.

I guess I could do some work-arounds -- maybe reserve one unit in the first purchase for use as an AirBnb, and reserve my own time in it when needed - instead of claiming it as a primary.Are either of you (or anyone) familiar with a finance product/loan that will allow me to purchase under $150,000 (w/ strong credit) and do much of my own work and live-in a portion as a primary residence?  

Thank you and be well-ShawnT Buyers aren't necessarily interest rate shopping they are shopping for affordable payments.

If you move to NYC, focus on maximizing your earning potential while investing in affordable out-of-state markets with strong rental demand, like San Antonio or Indianapolis.