I'm pretty new to real estate finance so I'm not sure if any of this info is relevant, but I figured I would throw that out there.If the proper route is a HELOC or construction loan, do you think it would be better to do that under my grandma's name (before she transfers ownership) or under my parent's name (after)?

Another one to throw into the mix @Antonio Malachi.

Just to throw out some numbers, according to Wikipedia, there are 43% of non-regulated apts in NYC.

I've seen so many folks crash and burn when they outrun their supply trains of investment and decide to throw in the primary to continue their pace of investing.   

Either way my wife and I still fully plan on doing our sell/move in duplex no matter what he throws at it but now I know to just nod my head and let the blanket criticism go on by. 

What's a good way to handle lowball buyers throwing their money around and demanding price reductions, even though its already an on-fire deal?

On a single family its not uncommon to have your tenants pay their own utilities so that could be throwing off your cashflow estimate! 

(Just make sure that if you don't pay it off, that you can get a mortgage and it doesn't throw off your Debt to Income Ratio).

Almost 3 years ago I decided I am throwing away money each month by giving my rent to someone else. 

Throwing good money after bad, but if you insist...You need to get a judgement against them in JP court.