My initial thought and strategy was that I could find an investor to purchase and do a double close type transaction where I would use transactional funding to purchase under an LLC, and then sell the LLC to the investor for my "assignment fee."

If your goal is indeed a cash-flowing investment, then you'll want to steer clear from any development where you'll be required to use their in-house management at fees from 30-45% of gross rent. 

You'd want to research to see if the fees/due are worth having MLS access.

.#1 - How are you structuring your fees, if not per property?  

Since the property management company charges first month’s rent placement fee for a new tenant, how should I factor this in with my Cash-on-Cash return - do I also lump it into cash needed?

@Sang PakBanks charge a loan origination fee to generate a mortgage.

Most title company’s will charge a fee for each draw.

You can then bill additional fees/utilities, etc as needed.

But I've chosen not to do a VA loan with them or anyone because they are more expensive than conventional with their 'funding fee'. 

I'm thinking this would be beneficial as I wouldn't have to worry about the tenant not paying rent, I would be building equity over time in a market it would otherwise be very difficult for me to enter, and I'd be able to minimize fees by finding the lowest cost property management possible (as I wouldn't need to worry about tenant screening, etc).