I’ve been driving around Harvest, Toney, and Madison to get a better feel for the market down here.

@Matthew Gangi is it possible for you to house hack somewhere within driving distance of Boston?

OR investing in high yield, low volatility property that is a little more crash-safe while you wait for the market to be more opportune for an appreciation play.

Not going to say that I am totally opposed to the cards/letters going out, but I'm not relying on them for leads - they are just another way to drive traffic to the site, where I can capture their pixel and retarget like mad. 

Those are stable skills that drive a stable income.

It says they hold the power to require occupants be member safe of a single housekeeping unit... so that’s my main concern.

I often break it down into the "five pillars" of protecting your assets.The first pillar is avoiding unnecessary and risky activities (don't drink and drive, insurance generally won’t cover your poor decisions) and take good care of your investments - these simple steps will help you prevent lawsuits before they even occur.The second pillar is a good insurance policy as that cover the majority of your exposure.

So if a property doubles in value you property tax will only go up by the capped maximum (I think 3% but it may be 2% - I used to know but do not really care about the 1% difference now).So at your income you will be challenged to find a place that you can afford with a safe reserve. 

I often break it down into the "five pillars" of protecting your assets.The first pillar is avoiding unnecessary and risky activities (don't drink and drive, insurance generally won’t cover your poor decisions) and take good care of your investments - these simple steps will help you prevent lawsuits before they even occur.The second pillar is a good insurance policy as that cover the majority of your exposure.

@Connor HeimMost small dollar units of property that you mention can be expensed under the 'de minimis safe harbor' by making an election on your return.A competent CPA will ask for a ledger or detail of the supplies account and fixed assets accounts to make sure everything is where it needs to be for tax efficiency.