This property is in pretty decent shape and I plan on updating the kitchens/bathrooms in both units to be market-competitive so assume an average quality apartment for the area. 

Randy, that’s what I’m thinking as now, if I’m understanding correctly, the past rent is a part of their bankruptcy and they only have to pay future rent.

I've got a friend who is buying his first single family home.  They are planning on putting a kitchen in the basement and renting it out to friends/family.  Its zoned as a single family home and has everything necessa...

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If I acquire a Victorian home with steep roofing, I am not even sure there are qualified roofers who can tackle the complexity.

In MA, property owners are REQUIRED to bring a property into a lead safe condition (called compliance) if a child under the age of 6 resides in the house/apartment. 

Hugely depends on the municipality, their work load, and the project's complexity.

Same process.. just more complex/complicated for large developments. 

It has potential to even fit 5 units, or four spacious apartments and one commercial unit (I think a soundproof event space in the HUGE basement would be incredible).

If you need to inspect units in an apartment building that will have to be arranged with the property manager and tenants, if you just need to check out the HVAC of an industrial property, that's usually a bit simpler to arrange.