I'd start with plans not a general contractor or HIC contractor.

Sounds like a tax planning opportunity for you and your tax pro.

I plan to move back to India soon and was wondering if at all it would be possible to remotely manage my properties from India (12 hour time difference makes real time communication a lot harder).

The terms on the HELOC, if you can find one, will most likely be worse than a cash out refinance term sheet I am planning to cash-out refi as much as possible.

It would require us to flip our site plan completely.

Do you plan to self fund or hardmoney/etc? 

If the guest has a valid point make some changes, and in the response acknowledge you we're unaware and plan to adjust.

I own, am planning to retire to the East Coast with my son and two little dogs.

So ask them to pre-underwrite your deal and give you a feel for what their best plan would be.

Some plans include house hacking, seller loans, flipping, creative deals, private cash, group deals, sweat equity, and government help.