I like the try and rent it anyways, but I can't seem to get around the Certificate of Rental Suitability.

As far as the seasonal question, I have friends who have airbnb’s in Chatt and the ones in the city seem to stay steadily booked throughout the year.  

It seems like he is not doing so.

I would probably stay away from FL - there seems to be some shakiness in insurance policies and pricing - but I am not an expert on that.  

Interest rates and appreciation seem to be the most important.

And based on my business, and from what I am seeing with market activity, it is still very much a sellers market for those type of properties so many investors don't seem concerned about these proposed regulations.  

@Francis Faucher and @Matthew Gentile Thank you both.As I continue to research the syndicate or JV models where I do not have to be involved the day to day operations and decisions seem most aligned.Matthew, appreciate the potential referral for accountants.

Seems like a cash flow vs appreciation market.

I see this Maryland form here that seems to be appropriate, but I am not eligible to file it because it mentions that it should not be used if filing it after 12/01/2023.

It seems like the income is significantly reduced when there is a mortgage but as a newbie I am trying to figure this out.Thanks!!