Having this mindset this early will pay off very well in the end!

In Worcester, I think your numbers are pretty close, but there are also a lot of Programs between Mass Save, and the City of Worcester that will pay for many of these things if you agree to an income restriction, or sell income restricted. 

Or their own file format, which opens their own software.I think I would have to pay extra for outgoing, however, over a certain number of outgoing faxes.

In general ground up ADU additions in SF zoned areas cost significantly more than they will appraise for.  

Like if they were required to pay 90% of their appraised value to purchase the property at the seller’s option?

I've been on the ground here since Sunday and head back home to CA tomorrow.

Payment is $450 cheaper ($4400 PITI v $3990 PITI).This is a house hack where the tenant is paying $2100 in Y1 with rent scheduled to increase to $2200.This HH is on a VA loan and I’d like to refi into a conventional loan eventually to reuse my benefits.

Have you ever built from the ground up and is there land available that would even make it make sense near you? 

My ultimate goal is to generate $11K per month in passive income and I believe I can do that by purchasing 3 more single family homes in my area and paying off the entire portfolio.

Why pay anyone for anything you can get yourself for free?