Another option is a revised Tenant-in-Common agreement, outlining property management, expense sharing, and a potential buy-out provision in the future under specific conditions.

rents are higher here by far one of the most expensive markets to live. lease price per square foots can go as high as $8 per square foot. if you live far away it'll be cheaper or you'll be living in a older unit. depends on your budget really 

@Joe Rinellakeep in mind MA (all states) has a state specific tax code beyond the federal tax code.

Without hearing the details its hard to make a specific recommendations, but frankly, being under rent control, that's a 'pass' for me. 

Making sure the rehab is done within budget and on time and inspecting the work as you go. 

No license unless you are listing your specific unit, not another within your 2-4 unit.Even if you do mid-term rental you still won't be able to get an AirBnB license. 

You wouldn’t be able to accelerate the entire $80k it would be more like 15-20% of the $80k depending on your exact property and as determined through a cost segregation study.If you’re not going to keep the property for at least 5 years or have a specific exit strategy in mind it may not be worth it to you. 

What specific features are you looking for in a property?

All I did was look at a property, run the comps, and got a reno budget, So nothing to intense.

This would be a great question to ask them as it's specific to you and your tax situation.