I don’t know how 2 people got 3 homestead exemptions but that seems like something the local taxing authority could catch pretty easy.

Now, people are fighting back to appeal the raises. 

It's a very local question based on the comps and active/recently sold inventory inside the community.

Understand you have great equity position but it is expensive, but more importantly  takes a lot of time and very distracting from other money making activities to foreclose.

Because Airbnb only makes money when the guest books on Airbnb.Hence, they want the price to be cheapest on their platform, so people book on Airbnb instead of elsewhere, and want their properties to be able to compete with hotel prices (even after cleaning fee and service fees). 

Because few people move in November and December.

These people are not necessarily in the business of lending money and loans from them can be negotiated in any number of ways.

Heck, some people might even pay more for the 'cool factor' of living in a 'small home'....I'd give it a go since you're a veteran of this RE stuff.

This is typically for most people not a DIY project. 

These minor details are the kind that distract people from the path of success.