Working with the city to find a solution.There is a similar situation near me where an investor bought a short term rental house, rehabbed it, ran it for a while, and then got in trouble with the town after a neighbor complained and the town said short term rentals weren't allowed in the community. 

@Kavya VeerapaneniThere is a market for short term rentals in Danbury.

It was held by the previous owner for a very long time, so I wouldn't be surprised if some basic facts about the house are incorrect.I was making an offer on a house a couple years ago and discovered that the owner was paying taxes on an additional house that was on the neighbors lot and didn't know it!

My idea to achieve this is to convert the studio into a short-term rental.I’m trying to determine if I’m forcing this deal to work by relying on the short-term rental strategy or if it’s a reasonable approach given the numbers.

It seems to me though your short term objective is to get the HOA to take immediate action on the roof.

but keep in mind CA has higher taxes and reg fees and I’m not doing more than 1-2 flips (short timeframe flips)  a year and many years do 0 flipsDo most flippers put flips into LLC Or in personal name (sole proprietor)  in CA (where you must pay $800 yearly plus accounting and other fees $300to $600+ yearly to maintain LLC) Pros for personal name-save on taxes accounting.

I'm interested in flipping, and short-term rentals at the moment to build good cash flow, then pivot into more of a buy-and-hold/appreciation play 10-15 years from now.

The Rise of Co-Living: As Airbnb Faces Restrictions, New Housing Models Win in Court 🏡⚖️Across the country, cities are tightening regulations on Airbnb and short-term rentals, making it harder for property owners to operate legally.

2) The minimum hours required are 750 hrs, but if running a short term rental, 100 hrs is supposed to be adequate, is that still true ?

I looked into the maintenance option years back to discover a trend of:  apx. 8% monthly fee which only included rent collection (everything else from maintenance to turnovers etc, extra, and poor reputation on repairs.)