$25k is only 4.16% of your new purchase price, heck of a deal.Thank you for your service and let me know if you want to talk any more details and run actual numbers based on your situation.

Because you can assume no Section 8 tenant has good credit, my leasing decisions had more to do with meeting each tenant myself to get a gut feeling based on their communicativeness, timeliness to showing, what questions they asked, whether they looked me in the eyes or avoided eye contact, etc.The downside of section 8 was the annual, then bi-annual, inspections. 

With you guys having a strong financial base you have plenty of options, you guys just need to pick ONE then go for it. 

If it is a contractor that is more organized they will likely do this already, if they are shooting from the hip "based on experience" they will likely just give you a total $ value. 

The information provided is based on my experience and industry knowledge but should not be considered legal, tax, or financial advice.

If the numbers don't work for expanding the building, explore the potential based on the current space. 

Diversify and leverage the best strategy based on the specific deal.

Don't change jobs or income yet.Once you do and you think you can manage the payments based on your new income, maybe once you get the rooms rented.Then if you want to switch there are plenty of opportunities. 

Hey @Aaron Ram, fellow Stamford-based investor here.

Quote from @Christian Styles: Hey Sam, I've used both Propwire and Propstream, they seem quite similar but propwire has a free base version and propstream does not.