We are trying to find a financially savvy way to sell and buy something new with the money from the sale.

I would find a good lender to research this product.http://www.fanniemae.com/portal/media/financial-news/2017/student-loan-debt-6546.html

I've considered taking out a HELOC on my investment properties but don't want to "over" leverage myself financially.

And some weirdos (like me) bake in a lot of "what would happen" scenarios when we're doing financial projections trying to model out a pullback and we have a bunch of money sitting in bank account earning 1% as a "just in case" reserve fund.  

I was inspired today by the most recent BP podcast, and as it states; I am training my self to think about "how  I can expedite  my goals to financial freedom VS making excuses and giving into fear and analysis paralysis. 

My goal with REI is that financial freedom and control over my future.

They're both for sale individually, but seller would prefer for both properties to go to the same buyer.  

Basically it would be financial freedom and to create a legacy for my family.

One to rent and one for an option to buy so I don't know why you would have to be worried about an installment sale.If you're worried about Dodd/Frank or the CFPB (scam that they are) work with a licensed individual or get licensed yourself.

We meet at Radius Financial, 600 Longwater Dr, Suite 107, Norwell.  7:00 PM on the 2nd Tuesday of the month.You've no doubt discovered how wildly expensive Boston properties are.