If this ordinance is still just a proposal, what happens to all of the STR owners when/if it does get passed?

I would confirm the other four owners and would not buy there is they were all the same family, it will just be miserable most likely trying to deal with 4 against 1 (unless they all hate each other).Your second concern is valid and correct.

After it's rehabbed, you could then rent both units and use the cash flow to offset another primary residence or potentially refi and use those funds to scale your portfolio.I wish this policy change was being talked about more because it unlocks a creative new strategy for investors in MA, since you do not need to owner occupy to do it! 

I'm a licensed commercial and residential agent and looking to acquire 28 units though owner financing. someone knocked it out of the park when they said your return is theoretically higher if you use financing vs cash.

We use Hospitable as our PMS for automated messages and calendar syncing, PriceLabs for dynamic pricing and market analysis, Minut for noise monitoring, Schlage Encode locks, Ring cameras, and the Google suite for shopping spreadsheets and owner monthly invoices.

If the underwriting goes smooth and I can have the cash on hand at closing, then maybe the owner wouldn’t care how the cash offer is funded. 

.: Quote from @Chris Seveney: @James WiseI was sitting next to a doctor at a conference who did a private money loan and lost $$200k then he did a jv deal where he became co-owner of a LLC, gave a personal guarantee on the asset and put money in the deal to buy it but didn’t put a lien on property so partner went and leveraged the assets as well and ran off and dr had personal guarantee.They then bought a property and renovated half of it then decided to knock it down….I had a successful shoulder surgeon ask me to list his apartment building that was under-performing.

Many houses and duplexes that have been fully redone as well as some that are still owner occupied that will get redone when purchased.

Are there no actual owners on BP? 

Too many small business owners get caught up wanting to look the part and spend money on things that do nothing for creating profit.