Most likely you will receive the most benefit from selling and deducting the loss but there may be limits to the immediate deductibility of the loss.

Keep in mind your homestead might be protected already (check for your state to see exactly the limits) and your retirement accounts also have their own protections.

They don't have to disclose flood zone here so you have to look it up individually, and some insurance companies have set up their own "surge" zones so either limits your choice of insurer or increases insurance costs in those areas.  

That doesn't sound very appealing to a developer especially 30 acres for a big project.Not all of the land may be developable anyways because of topography, streams, etc.First see if in county or city limits and land at current and future land use map and see what the area allows for zoning.

This is a declining market with 3 of the DC area jurisdictions recently passing legislation limiting how many days you can AirBnB a property, and limiting it to owner occupants only.

I would go for the best deal over limiting yourself to a specific type. 

I would like to get my license but I'm going to study a bit more before I do that.

That said, you can have a clause in your lease that has a limit on how long a guest can stay, but you cannot prevent daily guests, unless that guest has caused problems and you filed some kind of injunction against that person. 

If I wasn't able to find enough deals to keep pushing our limits and growing as an organization then yes, I'd consider looking in a new market with similar returns. 

Run it by your favorite attorney and then study every paragraph until you know it like the back of your hand.