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!

Hi Joel,I am interested in start doing the same as you to be using it for medium term rental (28+ day stays) arbitrage in GTA (as short-term rental stays (less than 28 days) are restricted).

Ensure the STR’s projected income comfortably covers new debt, even with conservative occupancy rates, and maintain reserves for market changes or vacancies.

For example, during a guest stay a furnished vase falls and breaks.

Even though we try to get to know our residents during their stay, it is probably impossible to truly personalize a gift for each of them.

We could have held off for a higher offer as the market stayed strong.

It all comes down to picking the right areas that work well with your personality and attract the type of clientele you feel comfortable working with. 

You can stay friends, but business is business.

I'd love to hear any thoughts on my strategy if you'd stay away from Multi-family or if that's the right call.

My biggest tip is to save way more that you make and then buy a 2-4 unit building and use a 203k or homestyle renovation loan to do some rehab and add some instant equity.Also, Network as much as possible and get comfortable approach any one and asking lots of questions.