If you want to understand 5-year outlook, I'd look for multifamily construction data in your area to understand what level of new units is and will be coming online in the near future. 

From my understanding, it basically means that you need an egress window.

Undoubtedly, the biggest regret is getting involved in the short-term rental market.

Brandon Turner's Rental Property Investing book is an excellent primer to understanding the happy path for purchasing a property - however in this market it really comes down to having bulletproof assumptions on rents/taxes/R&M/etc. as with rates as high as they are/inventory as low as it is, there is less cushion in your returns if you analyze properties with bad assumptions.

But more importantly ask for their rate sheet, if they can provide it, to understand, what the true interest rate is, the lenders spread, and the cost for that rate.More than likely if a broker is using the same wholesaler, it is because collectively, that lender is offering the most competitive rate.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

Working with the city to find a solution.Unfortunately, most agents may not understand the legal property status nor actually know how to find out what it is.

@Michael Plaks comments in this recent post on making sure the person you hire understands real estate sounds really relevant to your situation.  

I've spoken with the team and they understand that it is our job to meet your expectations once we've helped you set them and I can assure you that we will.  

What’s Important to me is understand the tenant pool.