If mgt headaches are a factor, make them MLOs. 

.$6,700 closing costs (which is factored into the loan) for a total of $145,400.Interest on the loan is %4.875Upfront costs are only $500 appraisal fee.$3,000 in escrow for taxes and home insurance.Monthly payment will be $1,375 which includes taxes and insurance figured in.The monthly rent is $1,650 so that will leave me a cash flow of $275.To remind everybody this is a SFH that I purchased 2 months ago and should be appraised at around $210,000.

When analyzing potential rental properties you need to factor in a vacancy rate of 10% and another 5% for repairs and maintenance. 

I don't think age was a key factor for us, but I'm grateful that we shifted our thinking and strategy while we have time to really benefit from the fruits of cash flow and long term appreciation, but I think attitude and financial savvyiness (sp?)

I neglected to include in my original post that the offers were all cash, so I do not believe the closing schedule would be a factor here. 

The variable of life span is hard to factor in to know if it is worth it to you.  

SOME (not all) lenders providing HELOC's will only require a 2055 drive by appraisal, while many will require a full blown 1004 interior appraisal and if there is any deferred maintenance that impacts health and safety, will require (Should...) it to be repaired before they will lend, bringing you right back to the issues associated with conventional loans/financing.

Some things to note that most are unaware of about BirminghamMedical drives our economy.

Drive for dollars.

That is not the case with conventional loans (another factor to consider in your analysis).