Nowadays many vacation homes are priced as STR businesses with profits baked into the price (with future guests expecting instagram furnishings).  

@Sat Palshetkar Welcome to the RE world and congradulations on jumping in.

Good luck on your RE journey in Costa Rica / in general!

Under NY state law he cannot now or in the future demand that I move the fence back onto the property line as I now have a legal claim to it. 

Once you trim it down to the better properties you can be pickier on deals in the future.

If rates go down in the future, we likely will have another run up in prices, so it might be worth it to Airbnb while waiting that out for a couple of years. 

Quote from @Spencer Elliott: Long story short, land is on loan and I’m purchasing a manufactured lot as a temporary home/future ADU to my final build.

Follow up re-engagement and appointment setting.

This way you can utilize the leverage if you plan to scale up in the future.

In a situation where you were doing an arbitrage (renting it from the owner, then yourself re-renting it to someone else) your costs to renovate/fix it up while you're using it would be able to be capitalized and depreciated by you once your rental was in service (available for rent to others).