I started communicating with them via text messages (they don’t seem to read emails) 4 months in advance about the rent increase and they assured the increase was fine and they wanted to stay.

I love all the debt funds where investors are saying "first position secured liens" - well yes that is what THEY invest in, but read the fine print that states "your investment is unsecured and not tied to any of the liens"....

I've used this insurance carrier for a while and I have a premium policy so it should all be fine.

How much is the fine?

Zillow is "fine" at best, but we all know there is a level of fudge in that.Maybe multi-family properties can diversify your portfolio and potentially offer better cash flow?

Everything was going fine until he realized he couldn't refinance in this current interest rate environment.

Quote from @Cameron Hamidi: My gardener went to remove a tree that was growing roots underneath the foundation, and when he sent me photos, there was cigarette butts all around the back patio and front of the houseSmoking outside the home should be fine (but not leaving the butts/trash).

Okay, fine.

Of course we all want cash flow but if the property is in a very desirable area with a high probability of appreciating quickly over the next decade or so I'm fine breaking even or even paying a little out of pocket every month.

What you use the cash out for, as long as it is for business purposes, is fine.