I turned my accounting practice into a hard core outsourced bookkeeper controller services and my wife is completely in charge. 

One thing you might think about doing is outsourcing everything in your business that you don't enjoy doing, or that isn't worth your time.

i was thinking of hiring somone for about 15-20 hours a week . right now the main thing i want outsourced is doing my paperwork and writing letters for me. i need a larger list for them to do

Maybe I'm missing something or maybe you're operating in a tough market where deals are hard to come by but if you're outsourcing the property management anyway, you could in theory invest in any market.  

I expect to either outsource the entire PM role at about 50 units or possibly start adding staff to take care of the day to day stuff.

As far as outsourcing PM to family, I don't think it's a good idea for me.

If you're like me and want to (mostly) outsource maintenance then Hemlane is a fantastic service but I think you need to have more than just a few properties to average out the high $34/mo. base price for the platform.If anyone knows of a better platform/service to use that handles maintenance for you I'd love to hear about it, but Hemlane is the only provider with this feature as far as I can tell.

This is one component of the business that I will never outsource to anyone. 

Everything else is outsourced.

We get prelims on the west coast in 24 to 36 hours. ( as they have been outsourced like everything else to the Philippines) No attorneys needed  LOL... we don't use attorneys on the west coast only time you do is if you have a dispute..