I will eventually sell the property and hence want to preserve the tax benefit.

The concrete put an end to that nonsense, and when the bank eventually got the house back in foreclosure they paid to have it removed and hook water back up.

I hope to learn and grow and eventually be able to do this full time. 

I put 25% down, and at that time we were thinking to keep this as a vacation home where we plan to retire eventually.

Eventually, the residents stopped paying rent and left, so the situation resolved itself.

I then moved on to non-owner occupied small multi family deals, eventually using private financing.

But in the same breath, having underwritten what must be thousands of deals now and learning to think like and underwriter, some of it eventually starts to make sense.  

Eventually it grew enough that the income started outpacing what I was making from going to work.

Of significance, I have a successful track record of bootstrapping and scaling a tech startup, which I eventually sold for $10 million after just five years and 100+ employees, all without any external investment.

I have typically seen in my own portfolio that tenants will put in a few maintenance request early on, and eventually settle in causing a few unexpected invoices.