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!

Raising the rents will not be as easy as merely sending out notices of rent increases.

For many, their downfall (and really what makes it so easy) is that it is a single-entry system. 

There's always typical question like contingency etc etc, that's easy to solve.  

Easy for guests to change if they get full during their stay, and easy for cleaners afterwards....

I personally think being a landlord in Chicago is easy and I have never had an eviction. 

A handy search bar in the upper right makes it easy to find previous discussions, blogs, podcasts, and other resources.

On the go coffee cups with lids, a big bottle of Dawn and the quick spray Dawn and much more.It isn't that expensive and makes it easy for guests.

I have to decide if im going to use a new injection of capital from the sale of my primary residence to:1) Hold in treasury bills at 4.5 percent until I find another property to purchase2) Pay off one of two existing mortgages, one at 3.75 percent and another at 4.5 percent3) Just find something to buy that beats either of those percentages on paper and be done with it4) Possibly loan out some hard money/broker it to a friend to allocateIts never an easy decision, but its a good problem to have.

It’s easy to get caught up in the excitement of a potential deal, but skipping this step can lead to costly mistakes.Getting your real estate license is also a solid strategy just realize once you have a license wholesaling may not be in the cards as its a very gray area.Lastly, since you're planning to buy properties for yourself in 2026, start laying the groundwork now.