The money aspects are harder.

But that begs the question: In order to guarantee a great tenant would you compromise on other aspects of your investing strategy?

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

It's quite likely that discharging a firearm within the city limits is a violation of a local ordinance, it is in my town, so check out that aspect.

Gina, I recently attended the FortuneBuilders 3-day event in Athens, Ga and it was definitely worth the information if you want to get started in learning about the different aspects of real estate investing. 

Some aspects of this include doing only the work that is required, periodic inspections and proactive maintenance.If necessary, pushing the eviction process as fast as the law allows.If there is damage (beyond reasonable wear and tear), retaining a reasonable amount of the tenants deposit.Quickly preparing the property after a tenant vacates so it can be rented again without delay.

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 we already own a lot of properties, we work to partner with cheap and skilled tradespeople saving maintenance costs.We are proactive in our maintenance so our tenants are happier and they stay on average longer than most tenant occupancy periods (which saves the owner on future leasing).We set up leases to end during summer months where we have the most tenants looking for new houses to rent so we can maximize rental rates.Even though we rent fast, we prioritize make ready repairs so that we can continually keep the property up to maximize rental potential and identify and get great tenants.We are proactive in our collection of rent so we evict faster than self managing investors.We perform inspections to identify how tenants are keeping the property to not renew leases to hoarders and people who break lease terms.We perform move in and move out inspections by video to document condition to charge back tenants on security deposits.For some investors, they are not as on top of all aspects of property management and they should get help (to improve ROI). 

Just kept focusing on finding and flipping the properties, never gave the organization aspect enough commitment.