I am actually investing in VA but I will see if I can talk to a lawyer to make sure we are working within the laws in VA.

Hey everyone, Jeremy Schultz, 24 years old, I’ll be finishing up school this July for law enforcement and don’t really know where I’ll be working.

To the OP I would suggest sitting down with an attorney familiar with Landlord/tenant laws in Massachusetts and get their input.  

Tried the same - Oakland is super strict - I have decided to add an extra bath and extra room to each unit of the duplex.

I see you are from Illinois and here is a link to their state website explaining that the property tax exemption is only on the primary residence:https://www2.illinois.gov/veterans/benefits/pages/real-estate.aspxHere is a breakdown of these laws by state:https://www.hadit.com/disabled-veterans-property-tax-exemptions-state/Thank you sincerely for your service to our country!

It’s a new ball game with the new tax laws and I am still assessing. 

The enrolled agent on this site also goes onto state there is case law (court decisions) that were in favor of cost allocation on Sch E, but the actual cases were not cited, and that if you were "aggressive and willing to fight with the IRS" the case law might actually support this.

This is also our first property in SF; we're doing all the research we can re: being landlords in a very strict county.

I recently have been  talking to my wife About selling this money pit that loan and taxes etc... are about $1900.00 a month and when my mother in law and father in law loses their tenants in a larger 3br 2 ba home we can rent from them for $2100.00 a month.  

Additionally I would also suggest you identify your metrics i.e. cash flow/appreciation/class of property/landlord tenant laws in the respective state and any other metric that propels you toward a specific goal.