Are there any potential risks or downsides I should keep in mind before proceeding?

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

City has so much potential.

In your scenario you'd have a potential tax event on that $200K difference.Here's a creative way to access most of that money tax free however. 

At the time, his offer was low, and I had potential plans for that space, so I turned him down.

I think too many people get into this and struggle for too long before realizing that they not been properly trained and potentially could have dramatically shortened the learning curve.   

I love it here because there are still positive cashflowing deals and lots of appreciation potential due to the strong job market, growing population, and major companies setting up shop here like Intel, Meta, Amazon, etc.

Seacoast NH, for example, has some great potential with short-term rental markets (Airbnb, VRBO), especially in towns like Portsmouth or Hampton, but the regulations can be a bit tricky.

They don't want the company to be potentially liable if an owner doesn't follow through with the inspections and repairs.After the GFC, we needed the capital investment or they would have had to tear down more houses than the thousands that they already have.

Basically, the further you get away from the city the more potential for cashflow, but you're also dealing with a different tenant base that may be tougher to manage.