@Josh Sterling
My initial thoughts reading your post were in line with what you and I have discussed a few times before. Scale seems to be the biggest hurdle, but as you basically said above, you are more or less there. At least enough so to justify a part time person.
I like the list, seems to be the exact things I would need as well. Though with only 11 units, these aren't task that trouble me and Sam too much.
Have you considered pairing with a couple other local investors, then, as a group, finding a qualified person to handle all of the collective properties? Each investor could pay a part that represents their portion of the total properties handled. It would be a better deal for the sub-contractor (person you hire) and cheaper for each investor. I actually have a person or two in mind that may work well in this kind of position, a stay at home mom like @Brandon Turner suggested. I'm not sure if the person in mind would want the job, but she seems like a prime candidate.
In my normal business, had I never stepped out of my own way and trusted other people to be competent, which they were because I paid them fairly, I would be a bottleneck to this day. Sure, I've had to fire a couple people and there have been a couple hurdles along the way, but none of it was too big a deal. I'd be much worse off if I would have continued to micro manage. I think, what exactly this person gets paid, and if they screw up a call or two every now and then, are the smaller picture issues that aren't even worth your worry to be honest. I think there is an opportunity cost situation here, that may be hard to quantify, but is very real. For example, if, tomorrow you spend the day showing a unit, posting a unit, painting something.... whatever, you may save yourself the cost of paying someone to do that. But, lets say, rather than that you paid someone else to do those tasks and instead you spent the day looking at deals and found your next apartment building. How much would what you do tomorrow, in this example, have made you in a year? Lets say you still own the building in this example 20 years from now. How much by then? Ray Crock didn't flip burgers and Donald Trump doesn't plunge toilets. I have tons to learn about real estate, which is why BS-ing with you is fun because you know a lot I don't. But one thing I found to be very true is that time is a finite resource. Maybe the only finite resource. When you spend your time doing things that are drastically beneath your pay scale, you are doing yourself no favors. One of my good friends once told me that 'money is the physical form of time'. (he's pretty much broke which is ironic and beside the point, but kinda funny) I like that metaphor. If someone is willing to sell you their time for $500 or $1000 a month, I think you should jump on it sooner rather than later. Whats 10 or 20 more hours per week of your time worth to you? If they work 20 hours per week for you for $1000 per month, you are essentially paying $12.50 per hour to buy your own time back. Sounds like a great investment to me.