I do not believe converting to condos would decontrol the building.I own a 4-unit multifamily in Union City and am considering condo converting it at some point in the future, though I do not think rent decontrol would be among the potential benefits of the conversion.

I have an appointment with a lawyer, but id love to talk to anyone that has had experience of converting in the past in Hoboken.

My challenge is that I don't know when exactly I will be able to obtain the STR permit from the city, so I don't want to convert guests too prematurely. 

In the event my landlord is interested in selling, I was wondering if I could add value in the short term by, say, converting part of the garage and/or covered porch into a bathroom and maybe a bedroom (currently 3 bed 1 bath).

I retired 10 years in and my wife 14 years into the journey. 85 % of my portfolio is 200 year old converted city row homes that are maintenance monsters and we still have enough cash flow to retire from our W-2.

It's all fun and games until your bank freezes and converts your line for any number of reasons that are in the loan agreement.

   - convert new RE purchase to STR.  

There are many reasons that adding a single ADU in southern CA is a less than ideal RE investment (i will post a list at the end) but the negative initial equity is a primary reason as the initial negative equity position consumes the initial cash flow and can take many years to recover.As for converting your home to a rental….

Inch by inch, life is a cinch."

MF with many garages to convert to ADUs, parcel splits, full on development, coop/tic with the resources to handle financing challenges, etc.To raise money in this market as a newby will also be challenging unless you can get it from friends and family.