Your neighbor s as Sean mentioned, have a lower tax bill likely due to the fact that they live there and there are laws that prohibit the tax assessor from raising the property values more than 3% per year when it's your primary residence okay, it's also fairly common for your tax bill to significantly increase in the tax year after you purchase it.

Quote from @Alex Silang: Stop playing around.

If you’re looking to build long term wealth, accumulate assets, take advantage of tax code, and benefit from appreciation, then play the appreciation long game.

In MA, you can usually get insured with Fair Plan with certain pets, but it is VERY expensive.  

And the reason why your "tale of two halves" will play out as you described.Demand:  This has actually been high almost all along, but rent growth hasn't materialized in response due to high levels of new supply. 

A few of my investors charge a point or two for an extension, every 6 months = 1 point seems fair.

Stick with what works for youWhat would you say is fair?

When an owner passes away, the property’s tax basis is reset to its fair market value on the date of death (this is known as the “step-up basis”).

Would it break fair housing laws to say we are not willing to work with the program since it's not a source of income and they pay on their behalf?

At the time it was fairly easy to find properties that needed enough rehab that you could really force up the ARV.