The most satisfying changes I've made is move out of tech management and back into just engineering roles, I sold my house in the city and moved to 5 acres in the hills where i work remotely for less money gladly, I've paid off everything, and now I have the flexibility to do anything.

That's awesome that you have that flexibility!

You could certainly reach this demographic, but it could also cost you substantially more than the return.For the money, your best bet is probably a dedicated website for your property with the key words that you want to convey.

Nothing is a sure bet.

Best bet is to carefully analyze the zoning maps and regulations or just call the town and ask.

Originally posted by @Mark Whittlesey: I would get a UPS Store (or similar) box instead of a PO Box.It costs more but is much more flexible (is an actual physical address, can receive UPS and FedEx etc.)I had a PO Box for a while and got rid of it for exactly those reasons. 

It's a stalemate due to affordability and either wages or prices give, I would bet the latter. 

You can get more cash, but you add risk and lose flexibility. 

Maybe a couple of them to allow for some guest flexibility.  

Hard money can give you more flexibility and faster closings, which are often needed for investment deals.