Next, I would absolutely make certain that you are in 100% compliance with every aspect of the required compliance regulations in your intended state of investment, in your case, I presume this would be Florida. 

Purchase a turn-key multi-family property that I can afford to put a down payment on with conventional financing in a decent area more suited to my price range.I know that I would need to analyze the cash flow from each of the deals in order to properly to determine which of these scenarios would be the best from that perspective, but I guess what I am trying to ask is which of these three strategies would be best in terms of other aspects of buy and hold investment?

Since 15 of the 18 units are occupied i began struggling with the contractor aspect as well and finding an appraiser out there because we would love to pick this property up.I definitely love the town-like feel of Hagerstown and Cumberland

Some PHAs have, in the past, basically gone broke to pay for certain aspects of their operations.

We have discussed the professional cleaning aspect as well and he agree verbally that when the time comes to clean if we are unable to pay for it he "might" go in half for it but we are used to his verbal agreements falling thru.

(Just off the top of my head people as an example)Now, look at each of those functions and what might be involved with such aspects and address them in your Operating Agreement or By-Laws.

A trust provides zero protection at all, and with todays technology, it is nothing for an attorney to find out the back info of the trust.

For almost every other aspect, landlords, rehabbers, lending, getting started etc...

I appreciate cautiousness in adopting new technology, but it seems to me anyone refusing to use PEX at this point might just be stuck in their ways. $2500 for a repipe is a decent price, though of course it is hard to say over the internet and without knowing anything about the house.

Having only one aspect such as land may not be sufficient in an equitable exchange for the economic benefit for the use of money.If someone has no management skills, no experience, no capital or income, and can't contribute anything to improve the land as labor, but has 1,000 acres and wants to borrow $1,000.00 that is not an equitable exchange. if any lender did lend in that situation it would be a predatory transaction.