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Please note the information provided below is a layman's definition designed to provide a basic understanding for the general audience.

So it is going to be up to what you and your CPA are comfortable defending if ever questioned.

This was the ideal value add situation, where I didn't have to change much on the layout.. mostly just design.

You could find a partner to help establish an LLC that rents out your property long term, then subleases on a short term basis (master lease is one that is designed for subleasing, it is a way many people pick up STRs without actually purchasing any property, they just find owners who are okay with them subleasing on a STR basis). 

You can usually get the zoning destination with the property listing, then look that designation up in the town's zoning code to see which uses are allowed there.Basement habitation - There is a concern that limited egress, fire and CO are major risks to bedrooms and habitation in general of basements.

I did mention two other things, but those were specific to the comfortability/uncomfortability of the roommates based upon her actions, which the lease does not mention anything about.Moving forward, I will include something about the roommates opinion in the lease. 

Today I'm more comfortable with free and clear property. 

Additionally, the owner is considering design plans to convert part of the upstairs into three apartments, adding further value and flexibility.I’d love to hear your thoughts.

I actually ended up working with a DFY arbitrage program that finds the right property, negotiates the least terms with the landlord, and even has an interior design department to set up your listing.