Hopefully that upfront diligence plus a healthy contingency budget would suffice to keep me out of that scenario, otherwise I would foresee a guaranteed loss, or underperformance at the very least.

Random example from this week:Sell at a loss or rent at a lossOn the other hand, if you are willing to put some time in by traveling to the market, spending time getting a network set up, screening dozens or even hundreds of properties, and taking the time to get set up right, you increase your chance of success.  

Masthope had been rumored to be limiting STR, but it seems they are keeping their eye on the fallout after the big court win in Lake Ariel - https://www.timoneyknox.com/reversed-short-term-rental-regul...

Heck it's so good I could manage a loss for a few months but I really think the cash on cash return will be 10% + first year and 20%+ 2nd year. 

I have learned that in today's world of information you do not need to limit your investment to just markets you live in or normally travel to. 

Private Money Lenders are going to be hard for a primary residence as it is an investment and typically they want to see a return prior to two years - also, the house would need to be purchased at a discount which would limit your options on a primary residence - now if you are looking for something that needs some work that you are planning on fixing up, it would be a little more feasible.

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Recent discussions in Bloomberg and the Yale Law Journal shed light on the challenges posed by traditional zoning regulations and offer insights into potential reforms that could benefit co-living arrangements.Zoning Laws and the Definition of FamilyTraditional zoning laws often define "family" in narrow terms, typically limiting residential occupancy to individuals related by blood, marriage, or adoption.

As well as limit you potential top end profit.

Looking to limit the amount of cash I need to put in (ideally under $10k) by leveraging different financing options @Eric Huntermark I think less than $10k down on a purchase price of $150k is going to be hard to find.