It would certainly be easier to just pay a bank, lawyer, CPA, bookkeeper, or property manager to receive the checks and deposit the money.

However, the trade-off we made switching to a property management specific software was still well worth it, even if the accounting/bookkeeping portion of it is not as user-friendly as QB.Not sure if that helps answer your questions, but at least gives you a few things to consider.  

Payroll, bookkeeping, etc can mostly be done remotely.Here is a great list of questions to ask a potential accountant:http://www.biggerpockets.com/forums/51/topics/70447-questions-to-ask-a-cpaAlso check out the www.NAEA.org page in your search.

Cleaning, Maintenance, posting ads daily/weekly to fill spots, bookings, book keeping, maintaining the relationships with marina, restocking, scheduling, praying the weather is warm and sunny so it rents (life shuts down around here when there is rain/tropical storms/hurricanes in the forecast).

The safe harbor applies to amounts paid during the tax year to acquire or produce what the regs call a “unit of property” (UOP), you must meet these requirements:(1) at the beginning of the tax year, the taxpayer has written accounting procedures treating as an expense for non-tax purposes amounts paid for property costing less than a specified dollar amount (which will be 2500 for you), or with an economic useful life of 12 months or less;.(2) the taxpayer treats the amount paid for the property as an expense on its books and records in accordance with its accounting procedures. ( do this on your bookkeeping software or whatever you utilize)(3) the amount paid for the UOP doesn't exceed $2,500. as substantiated by invoiceNote: The cost for the Unit of Property includes l additional costs (for example, delivery fees, installation services, or similar costs) if these additional costs are included on the same invoice with the tangible property. 

Need to choose a RE diy friendly accounting software that will allow me to do the book keeping on multiple businesses (ie partnerships), ie scale.

A bookkeeper :). 

I will be extremely diligent with my bookkeeping and I like the security the LLC gives if ran properly.

(Our multi-tenant buildings typically get reimbursed by tenants) The scope of the work includes invoicing, bookkeeping, paying bills, oversight on light repairs and maintenance, and communicating with tenant requests. 

Now my dad teaches me about the book keeping, the state tenant laws, and more.