Hard Money will usually "balloon" (that's where the mortgage is due in full) after 6 months.  

The little time I had with him I cherish and he is intensely missed every day.My primary career has been managing various claims from habitability to slip and fall (personal and commercial) workers comp to dog bite and private passenger auto/trucking with attorney involvement, so I’m not shy nor am I intimidated by these life sucking vampires, lol.

I think my only option would be a private money lender, does anybody have any thoughts?

The only comps that an investor may have knowledge of that the appraiser does not will be private sales, FSBOs that are not in the MLS.

Ok, so using the rental calculator it is showing my cash flow at $19 per month, but I can't manipulate the numbers to show the correct balance on the mortgage.

I also welcome perspectives on utilizing a HELOC, other financing options, or keeping my primary mortgage-free.

The issue now is that I'm not sure if I bid on a second mortgage or if there are multiple mortgages on the property.

I'll second @Evan Demchick's suggestion - you may have an easier time doing the deal with hard money/private money/your own money, then after it's rented for a while any bank is much more likely to give you a loan.

I have never used an FHA 203(k) loan myself, but several years back when I used to do mortgages, I did sell a few of these to my clients. 

what if the laws changed and that impaired your ability to get income you needed to pay your mortgage?