You start thinking about how to scale this...its now a P/T business, you learn more and decide that MF creates more cash flow than SF per $ spent, you may have to pay higher financing costs once you go beyond 10 loans (including your home), more time w/ more properties, etc....all lead you to think of a different strategy.This is where I started into small MF because I wanted to leave my corporate job for good and MF could get me there quicker per dollar saved and invested.  

We currently have 1 rental property that we've had for a few years but are really looking to scale up in the next 2-3 years.I've also been looking at some other areas like Lynchburg, VA and Charleston, WV as their cash flows for buy and holds seem more attractive.

The economies of scale with multifamily far out weighs buying SFRs.

It just seems like they need to be done on a fairly large scale to justify all of the headache. 

The work I need done is on a much smaller scale than what yours sounds like but I feel your frustration.Good luck on your project!

The park is in Beaver Creek and it a pretty large scale development.

Is it worth it to hire a part-time bookkeeper, at what scale would I need one and where do I even find one?

Get a feel of what the market is demanding, a feel of dealing with sellers, negotiation skills and then scale up.

I'm really interested in getting into larger scale buy and hold deals, maybe apartments or commercial.I'd like to hear hear what some more experienced investors might do in my situation to leverage the initial equity i've built up into some bigger deals.

It actually might save you some money as the turnkey companies are selling you a full package.There are landlords such as myself that for some reason have decided to scale back or change directions in their investing and would be happy to sell a couple of properties with good tenants in place.