Also, I had to set it up with real estate specific categories and I'm not an account / bookkeeper so this go really messy. 

Having a system tailored to real estate investing and doing everything I would want a bookkeeping system to do has made the financial information I have much more accurate and timely.

It's also a good time to consider what will work best for you when it comes to bookkeeping.

While the bookkeeping will likely be complicated, is the accounting/taxation on this STR based on 100% STR income/expenses allocated 100% to business and general house expenses (mortgage, utilities, depreciation etc) pro rated between STR/personal residence based on sq footage?  

I'm currently a payroll manager part time and have done other bookkeeping / management jobs, so it was recommended that maybe I find an investor who is needing help managing their books or payroll. 

Did you create an LLC for the purposes of operations and management, i.e. book keeping, income/expenses, etc.?

We usually bill our owner's via cash rather than accrual (IE our July owners statement for an owner has their July revenue minus expenses paid in July) but the owners get confused when the cleans don't line up to the stays, so had to train our bookkeeper to include the July cleans on the July statement even though that invoice was paid in August, which is different than how all the non-cleaner invoices are handled.

I agree with @Joe Villeneuve.Real estate investing requires a certain set of service providers (RE agent, PM, lawyer, accountant, bookkeeper, contractor, sub contractors, handyman, etc).

As for accounting basic book keeping can start around 100 bucks a month at a lot of places. 

An LLC could simplify bookkeeping and structure your growing investments, but its main advantage would be in organization and liability rather than immediate tax savings.