Would prefer to do cross collaterilization with a free and clear property I own to decrease out of pocket upfront expenses.

Since first time homebuyers cant/wont buy occupied properties you are only competing against other buy/hold investors which decreases overall demand. 

Maybe If Walmart puts in a store, they expect that area to grow & Walmart did all research for you.My cities population is decreasing. 

. - Mortgage rates also fell to another record low in the MBA's survey, as the 30-year fixed rate decreased to 3.43%.

It is a monthly fee based on the original loan amount so it does not decrease as the loan amortizes. 

I guess you really need to do the math on what the decreased value is for 5 units and compare that to what it will cost to add the 5th unit, how much extra rent you'll get and how long you plan to hold it. 

You'll end up paying (in time, cash, or both) doing it yourself first, but consider it paying for the education, then maybe you can transition the property to PM and still make some cash (rent increases, find ways to decrease costs..etc.)

If the state doesn’t get their political act together and/or the decreasing middle class continue to move out in droves, we’re all toast up here.

Purchase price and rental income typically decrease as you move west (Millsboro, Georgetown are somewhat central with Laurel and Seaford being the western side of the county). 

How much of a decrease are you willing to take before you adjust your expectations or holdings?