Boston remains a top multifamily market, driven by its world-class educational institutions like MIT and Harvard.

To make the losses non passive so they can offset your business sale gain, you’ll need to materially participate in the STR and ensure the average stay is seven days or less.

**Ownership & promote structure:**     What feels realistic in terms of:   - Percentage ownership to land contributor vs. cash/equity contributor     - Developer promote / waterfall so the sponsor is properly incentivized, but the landowner still participates in long-term upside?

Perhaps the less eyebrow raising method would be, if your goal was a more hands-off approach, is to leave it as an str the following year but under full time management, once your material participation hurdles are met in the previous tax year. 

I use that a lot in my daily life as a broker in Reno, NV educating clients on investment decisions and in my own rental acquisitions.I also worked for an institutional flipper for two years (Wedgewood) as a project manager and flipped 70-some-odd houses for them which really helped me cut my teeth on construction management.It really depends on your strategy, but ultimately it's playing long.

As Aaron mentioned, the key here is to materially participate in your rentals, and sometimes that can be challenging to do.

Acquisition Fee: biggest driver I see (and apparently all institutions too) is level of acquisition fee.  2% or less is ideal. 

Also, if your short-term rentals qualify under material participation rules, you can still use depreciation benefits to offset W-2 income regardless of whether the property is in an LLC or not.When you own in both states, you don’t necessarily need a separate LLC for each property.

@Amit Shukla the STR loophole allows you to take losses from passive investments and deduct them against active income by material participating in your property. 

If your average stay is ≤7 days and you meet the material participation test, you can still treat it as an active business.