I am not surprised on listings having inaccurate info.

Ask your employer if you can have your pay split up into three deposits, one to investments savings, one to your checking account for personal use on a daily basis, and one to an emergency account you can tap into so you don't have to tap into your investment savings.

I'm surprised someone verbally told you you can convert back to a duplex and didn't tell you that you must get permits.from what you are describing it seems the town gave you a hard time because you didn't get permits, I don't know that you have any legal standing to go after the town,  again, I am not an attorney 

AirBnB has been the biggest surprise. 

You will be surprised.

100% nightmare tenant that will likely get surprise roommates and a zoo of unauthorized pets while they live there and then claim "oh I didn't know that was against the rules".

Since you mention you have a partner, setting up an operating agreement is key to defining roles, responsibilities, and profit splits to avoid conflicts down the road.A few key tips to protect yourself:✅ Use separate bank accounts and keep finances clean✅ Get the right insurance (general liability + builder’s risk)✅ Have a solid contract with contractors to avoid surprises✅ Always verify permits and city regulations to stay compliantI still strongly advise you to work with local professionals, I’m happy to point you in the right direction!

For example, should we focus on acquiring one high-quality property in a strong market, or would it make more sense to spread the investment across multiple lower-cost units in emerging areas?

I am surprised that @Noah Wrights clients aren't as concerned with that.

Whether that's for routine maintenance or emergency repairs.