Jake, mad respect for starting at 19.

Even if the current tenant wants to stay and signs a lease at the current market rate they can get mad in the future and say that we violated the City rental law's limit on annual allowable rate increase and they would win in local court (based on what I'm hearing from other people in the market). 

2) Employment & Economic DriversWhich job sectors are primary drivers in each of these regions?

@John B.Smart move thinking within driving distance, but for a 1031 into a 4–10 unit the bigger drivers than state taxes are real NOI, insurance, tenant demand, and resale strength when you recycle capital.

The reason we still feel bullish (not reckless) is that there are several obvious levers the prior operation didn’t really pull: delivery/pickup was not executed well; we’re partnering with owner.com to rebuild the website/app funnel and online presentation (not a plug — just something we believe will move the needle),delivery radius will be supported via Uber drivers (~15 miles),alcohol sales were only 1–3% previously because the old location didn’t have an actual bar and there was basically no signal that they served alcohol (no mixed drinks, no “bar energy”),the new space has a fully remodeled (2007) kitchen/dining, plus a legit outdoor eating area, and we’re reopening there in April.  

Investors who’ve actually run the numbers know better too.What makes this niche interesting isn’t just the demand (which is strong), or the margins (which can be excellent), but the control you have over the outcome if you build it the right way.In a phased development model, the biggest value drivers happen long before the first guest checks in:choosing land with the right zoning pathdesigning infrastructure that can scale without reworksequencing buildout so the project pays for its own growthmatching site mix to real demand, not assumptionsbuilding a guest experience that earns repeat stays, not just bookingsOnce those pieces are right, the downside shrinks fast.You’re not relying on one tenant type, one lease structure, or one rent assumption.

Even if the current tenant wants to stay and signs a lease at the current market rate they can get mad in the future and say that we violated the City rental law's limit on annual allowable rate increase and they would win in local court (based on what I'm hearing from other people in the market).

Appreciation still helps long term, but it’s more of a bonus than the main driver.

My only concern is down the line if I have to evict them would they get mad and give a hard time?

Which will no doubt make him mad and may even result in them moving out.