Hey Rob,
We're buy and holders like you. My wife and I have now set up and run 9 properties for ourselves and 2 for my parents. I've managed a portfolio of over 50 properties. I list my credentials so that you'll believe me when I say that while the process gets easier, the tenant needs never change, and you never get more time. We brought property management in at property number three and have never looked back. It has been a game changer to have someone else manage repairs and tenant issues. It has also allowed me and my wife to focus on acquisitions, managing our rehab teams, consulting with tax, legal, and insurance advisors, and most importantly, getting out of the house to spend some of that cash flow once in a while!
To answer all of your questions:
We are so very glad we got into the rental business.
I was able to quit an absolutely miserable day job, and now I own a furniture making company, Barndog Mill LLC. The extra cash flow from rentals made this dream possible.
I suggest getting property management after property number one. I plan to always keep one to manage ourselves, so we don't lose touch with what tenants want in a property.
As SFR section 8 and mobile home landlords, the stories are too numerous to convey. Our first ever tenant ended up in an eviction, and we quit for one year until we pulled ourselves back up by the bootstraps.
Hope this helps and brings a little encouragement. Keep solving problems for people, and you'll keep making money. You are putting a roof over someone's head and filling a valuable need in society. For that, there will always be a need.
Best,
Mike