When is self managing too much? When do most investors decide to turn over property management to a company? What are some success stories about turning over properties from self management to property managers?
Too many variables to really put an answer on this. There are LLs on this board a la @Steve Vaughan that successfully self manage a lot of units, and there are LLs on this board that screw up a single unit. It is really dependent on the individual, their KSAs (knowledge, skills, abilities), their interest level, their geographic proximity, etc. Some people want strictly hands-off and are fine with less return in exchange for doing nothing. Others want to maximize their return and don't mind investing a few hours into their investments in order to make it happen.
Most people will find long-distance self-management difficult, and that's a natural for putting a property into PM. If you're too soft to deal with tenants, or unskilled at marketing your property, then it doesn't matter if you live next door to the property - you should probably put it under PM. Personally, I prefer to manage all my properties because a) no one cares about them more than me, b) there's no PMs in my town worth a crap anyway, c) my properties are fully renovated and rent so fast that PMs would do virtually no work for their pay anyway, d) I'm a control freak, e) I make more money.
As said, that's probably a tough question to ask. I can only speak from my perspective, but I want/like control and am always leary of people that control my money. But I also value my time....time is what I want anyway. Money made from REI just happens to be the way I intend to have more of it to do what I want.
So for me, if I can, it will go something like this:
1. Continue to accumulate property until I can semi-retire or fully retire from my cubical environment.
2. Once I've done that, I have more time to manage so I continue to accumulate property until...
3. Five percent of my gross rents are enough to pay my own employee that I train to manage all my apartments. Better yet, potentially hire two people so I have some redundancy should one of them quit.
There are some potential pit falls with that plan (mainly there's a chance that 5% isn't enough to match the work involved w/ X number of doors. But that's my plan, only at 11 doors right now so managing them isn't always ideal but is doable with my current job.