If you are meaning you'd like your Realtor to spend marketing dollars targeting buyers in other areas, you'd need to discuss that with your Realtor.

I 100% endorse adding in the escrows for taxes and insurance to set the buyer/borrower up for success. 

Managing your budget is basically advertising as needed.

Basically, more than a certain amount of STR and MTR in the same building were considered a hotel and I would have had to have 24/7 staff on site.Were you able to get around that with the local municipality?

When picking a market, I would look for things like population and job growth, rental demand, and economic diversity—basically, is the area attracting people and businesses?

They will surely be happy to add you to their buyers list! 

He also mentioned that, now that I have seen evidence of water intrusion, I will have to disclose this to future buyers if I don’t address the issue.My question: Should I reach out to the previous homeowner?

But if it’s a sale, some buyers might be okay with a few unfinished details, especially if you disclose them upfront.

I suggest the buyer at least get an estimate of the potential tax savings. 

@Nathan Gesner  is on point yet again, start with your basic estate plan first just like he did.