(mis) Adventures in Property Management

Six years ago, my wife and I sat down for the first of many closings on real estate deals. Unbeknownst to us at the time, we were about to embark on an exciting, frustrating, rewarding and endlessly stressful adventure, which if known to us at the time, might have given us pause in that moment.

You see, we started this adventure as renters ourselves. That first closing was for a stately four-family Victorian, featuring a massive and well appointed owner unit which would be our first experience with home-ownership, at the same time as launching our dream of a vast real estate empire, generating passive income as we enjoy financial freedom, and a guaranteed and stable future... How rewarding it was going to be to rent to others, just like us.

Six years and several closings later, our quaint little misconception of the life of the landlord, still makes us laugh at just how naive we were...

After the first year I was absolutely certain I had heard and seen it all, but every year the stories just get better and better (or worse depending on how you are looking at it.) After swapping a few tales with family and friends, and registering their complete disbelief and ultimately the humor of these outlandish circumstances, people and stories we have endured in our trade, I decided the time had come to start cataloging this crazy adventure that we call Property Management.

I am here to tell my story, not to educate other prospective or current landlords on how best to perform their trade, but over the years I have made more mistakes and learned more hard lessons than I care to admit, so undoubtedly there will be shreds of wisdom in my tales from time to time.

If I could go back six years to those two naive kids about to sign what would become the rest of their lives, what would I say to them, knowing what I know now?

"Good Luck.... you'll need it! MUAHAHAHAHAH"