Fast forward to Nov. 2020-The City of Daytona started issuing fines up to $15k for even POSTING on any STR site, even if you never rent a single day. 

It wasn’t until I made a profit that it was an issue.

However, the returns could be significant due to the desirability of the location.33020 (Hollywood) - This part of Hollywood, FL, has varied real estate offerings and is relatively more affordable than its more famous neighbors.

An appraiser is typically going to rely exclusively on the sales comparison approach and hopefully find relatively similar comps to compare the Subject to. 

This is a "hire someone" but getting someone to look at it before we need to put in an offer is tough in the local market and the contractor we usually use is unavailable do to family issues for the next two weeks.  2) Will it matter which direction the new stairs would run up the second floor in regards to the direction the joists run? 

There's absolutely no issue in asking.

He is now selling the property and the new buyer says she cannot find an insurance company that will issue her a policy because it doesn't have central heat/air.

Your quotes should address these issues if they are present.Good Luck!

My guess is he has other things going on and having mental health issues.