Based on the history of the property I would take advantage of the situation once you have completed your due diligence and make a much lower offer.

You are definitely at an advantage with your professional expertise.

Significant advantages are commercial valuation models w/value add plays and scale, difficult for small players to enter this space w/o a lot of capital and experience on their own.There are many niche areas as Dan mentions.  

The only advantage would be the Option Fee and the consistent income regardless of performance and not being responsible for maintenance costs.I think that you will have better luck finding motivated home owners who need some quick cash and will sign a lease with option to buy at a low enough price to put you in the middle.

5) Any programs out there that I can take advantage of?

I just read the Millionaire Real Estate Investor and he talked about 15 year loans being more advantageous in the long term (allowing for more wealth with fewer properties owned).  

@Ben Leybovich Yes, I'm another CA investor with tons of money to throw around in mid-west market and being taken advantage of by local PMs, contractors and tenants.  

For example, in original loan estimate there was a lender credit of 500 plus now it becomes 200 credit and even that is used to offset much higher appraisal related charges 650+150(investment cash flow schedule)And to be clear, I made it clear this is investment property upfront, not like I want to take advantage of cheap government money by pretending this is a primary residence Anyway, this ranting was partly due to dealing with them and with insurance along the way accumulated enough negativities and it just pushed me over the edge even by smaller deal surprise at final closing statements.

Control and RollWith the owner being elderly - it would be best to discuss your proposal with their personal representative or relative - shouldn't negotiate with elderly seller - you don't want anyone to think you are taking unfair advantage -Your offer should be that you will offer to purchase the property subject to an assignment to third party - you will need right of possession - a long study period.

It'd save you some money (since some HELOCs charge loan fees and early termination fees) and will be better for your credit.Getting a HELOC takes about as long as a mortgage now anyway, so I can't think of any advantage why you'd want a HELOC first then a mortgage, unless I'm missing something?