We added square footage and all the decks and now operate the property as a short term rental with massive success due to the team handling the management for us as the operators.

On the demand side, both the number of new deals signed and the leased square footage are below pre-pandemic levels.

Square footage?

haven't read the above posts, but I'm sure its been mentioned refinishing is better and cheaper. refinishing the same square footage should cost less than half that, as least on the prices I pay.

However, when you sell it, will the assessor consider the additional square footage in the assessed value or only use the permitted square footage? 

Nearby nice 1 br apartments of similar square footage are renting for $1750.  

Some larger houses also lend themselves to being divided (though Victorians are notoriously hard to heat & maintain they often have a ton of square footage). 

Provide a similar square footage, number of beds and baths, and look for similar properties.

Generally speaking, as long as you are not adding square footage or additional plumbing fixtures to the property, no permits are needed.  

It's listed for $186,000 (I'd like to be closer to $150-160k). 4 units - 2x3/2 and 2x2/2, total square footage is around 5400sqft.