painted it out and new carpet and light fixtures and blinds, the usual cosmetic " lipstick". 

Call it how my DNA works.People do not do their own surgery; you find a qualified doctor even if it takes more than one opinion to find someone.

It probably needs $40-50k in mainly cosmetic upgrades, but the un-permitted areas could make selling difficult.I'm not familiar with this area, whether it's historic or not, or if it would be difficult to get permitting for additions done 60-80 years ago.  

If you're lucky, you might even find a few brand new appliances with cosmetic damage.

What are your anticipated rent after the cosmetic rehab?

Mostly exterior cosmetic improvements, some interior improvements including flooring.

Purchase price: $410,000 Cash invested: $87,000 16 unit apartment building needed cosmetic upgrades in common areas and units What made you interested in investing in this type of deal?

For a first time house hack I generally recommend something that doesn't need a ton of work or something that just needs cosmetic updates.

If the property has undergone a "cosmetic" change IE: windows, paint, bathrooms, floors, kitchens it would most likely slide under the radar and not fall into HST provisions.

They are 60+ years old and waiting on a major leg surgery and have various health problems.