The question I am wrestling with and I am literally out of my mind thinking about it - shall I rent the current home (A) and hope that the property appreciation will make up for the lost savings and more (build a asset and income stream over time)  or should I sell it (A) and invest the proceeds in (B) and bring down the monthly expense. 

That initial message was  a "stream of consciousness" to make the scatterbrain thoughts real.

The owner from talking with him is more interested in unwinding his estate and creating an income stream for grand kids which is why  we are thinking this may catch his interest. 

I assume this is a multi million dollar deal.the builder of course NEEDS YOUR equity to get his loan.. now the good news is if he  can get a loan means he is somewhat to fully qualified.. you can do a participation mortgage in second position calling out for an interest rate and a bonus you just put it right in the note.. or lets say your lot price is 500k.. you simply write your note for 650k plus interest.. this assure you of profit.I would not do this though if you have no means to step in and complete or cash out the first.. nothing is worse than taking over a build project from a builder that failed mid stream

What you have suggested in the OP sounds good, but rest assured if there is an incident, the victim will sue the "deep pockets" landlord before the "blood from a stone" tenant. 

Recently I have been considering investing in SFH or small multi-family properties in Vermont with the intent to generate a rental income stream. 

Find a PM that has some other units in the area so they can add 300 bucks more a month to their revenue stream.

I couldn't even ask my Dad to help (his blood pressure isn't great) for fear of his life. 

So birth certificate, certificate of live birth from hospital... social security card... blood type... organ donation later....

You try stuff and if it fails (and aren't wiped out), you learn from your mistakes and try something different.Now the question becomes the best ways for me to increase my passive incomes to create this income stream I need (the wellsprings of cash that outrun my growing expenses [healthcare in old age] and inflation).