For this reason, I highly recommend the 2 BR option over the 1 BR.  

Looking for a bit of insight as to my options on financing. 

I know this is most individuals’ issue and understand that there are other creative financing options, but I find myself stuck in an infinite loop of needing funds to invest so that I can raise more funds to invest.

@Francis Faucher most of our Canadian clients set up an LLC, which I beleive offers better tax options than a C-Corp.

Even with no devices turned on the appliances still have zombie power drain of some sort.

Are there no other options?

If the rent is deposited into your account then you have accepted payment.I use apartments.com and zillow to handle payments - they allow you to block payments.This won't help you this time but in the future your lease should specify how they are allowed to pay rent, specify payment options that give you control over the payment.

Cash out refinance puts the cash into your hands and money is power and it can be kept in a savings or another interest earning account to offset the mortgage rate.

The lot is 3x the size of the other option and the home has very high potential for value add.

If you're going to stay in Westchester, you'll have more options on the market this time around than when you first used the househack strategy.