We did get one quote from a local bank which aligned with your example, a 20 year with a variable rate.

A HELOC is a variable rate too.  

There are too many variables.

These are different models and projections that are affected by four key variables: vacancy, rent, interest rates, and cap rates.

Too many variables!

Accounting for multiple variables such as the one's above will give you a more accurate number of what the unit can produce. 

For your CoC%, do you use the same variables I used on my example?

I assume the renovations also reduce variability in the mechanicals/variable expenses.- 5% for vacancy, maintenance, capEx, 5% for management fees (live in, handling myself)So - on the low end: Valuing rents at $6400 (with one of them being my live-in)Monthly cash flow is -$215/mo fully baked ($6,400 income / $6,615 expenses)5 year annualized return at 26%Purchase cap 4.17%CoC: -1%50% rule: -$277Assuming a 4% YoY increase in value, the sale profit after 2 years and avoiding Cap gains is $338k/52% returnOn the high end:Valuing rents at $7000 (with one of them being my live-in)Monthly cash flow is $2645 year return: 27%Purchase cap 4.79%CoC: 1.25%50% rule: $72Assuming a 4% YoY increase in value, the sale profit after 2 years and avoiding Cap gains is $350k/54% returnWhat I'm struggling with:Is there a way to look at it qualitatively and quantitatively as a space "I'd really enjoy living in"?

If I put this in the stock market, I would need to make a return of 3.14% to match what I’m making in rental income.Some variables include: fluctuations in the NYC rental market and value that properties may appreciate, increasing NYC taxes and condo fees, fluctuations in the stock market, maintenance costs that will be needed in the next few years that will not do much to increase the value of the properties.I am not interested in leveraging these properties to buy a third.

If I put this in the stock market, I would need to make a return of 3.14% to match what I’m making in rental income.Some variables include: fluctuations in the NYC rental market and value that properties may appreciate, increasing NYC taxes and condo fees, fluctuations in the stock market, maintenance costs that will be needed in the next few years that will not do much to increase the value of the properties.I am not interested in leveraging these properties to buy a third.