you may find it beneficial to avoid paying lender fees over and over again, on 3 properties though if you go with a lender that doesn't charge a ton of junk fees then you'd save doing it separately. 

But if you're going after DSCR loans, it doesn't matter if you go the traditional lender route or not as long as the terms work for you. 

If after all expenses it cashflows then yea that would be the best option for you'll be able to sell the land, if it doesn't then hookups might be a better option (With the big assumption that there is demand for that in that area) 

It doesn't sound like any of this discouraged you, and I trust that things will get better!

It doesn't matter if it was by one of them, both of them, the dog, or a friend.

There may be pent up demand but the data doesn't show it. 

There are so many rentals in the area, probably on shared wells, so those people have either decided the STR use is okay or they are comfortable risking it.My intuition is that any actual disagreement over water usage could be handled with the other owner; but the risk would be if the other owner just doesn't like the STR and wants to use the well agreement as a reason to demand it be shut down.Any advice would be greatly appreciated!

Thank you so much for the reply I’ve been writing down by 2025 goals just because right now isn’t my time doesn’t mean that my time isn’t going.

It will continue to go up until it doesn't.

Just because you don't have the money right now, doesn't mean that someone with money won't partner up with you if you have a good deal.