No issue with the city since lease is 30+ days.

The city has great macroeconomics - population growth, job growth, and lots of companies choosing to move and develop here like Intel, Amazon, Meta, etc.

I believe Alexandria city allows it but portions of Fairfax county do not allow it. i would go option 1 personally. 

@Jesse Streng Great that you want to invest in the Detroit area but I encourage you to come to the city and spend a weekend here to get a feel for the market.

What if the city finds out? 

Rare do I hear of recommendations but I do hear people asking.I would think in any big city you think about, a visit to a local NARPEM meeting or 2-3 visits would be a great idea. 

.: Quote from @Don Solt: Hi folks, As the topic states I'm looking to learn everything I can about the City of Philadelphia and its real-estate market.

Quote from @Brandon Foster: Hello Ryan,STR is do able in the north county area but there are a lot of rules and regulations.The city of Oceanside right now will not allow anything STR unless it’s west of pacific coast hwy.This is changing a lot too so you need to be aware of that in your plans.Carlsbad is super strict too but there are some condos that are still available to do STR in.Medium term rentals are as safer bet but way less profitable.

Our process server charges $40 within the city limits.

Our logical process:1) Use Neighborhood rankings to narrow down area of city you want to invest in2) Focus on getting to know that Neighborhood(s), so you know the good & bad streets, block-by-block.3) Be patient to acquire properties on good streets that meet your buying criteria.Our rankings are done with a "bell curve" approach.