The current layout is  very awkward and is a poor use of space, but could be tremendously improved by just swapping the tub and shower locations/orientations, which I imagine would drive potential costs up a lot.

The only full bath has a poor layout due to it being narrow and having a sloped ceiling that follows the roof line.  

Heavy - New floor plan layout, structural changes, MEP upgrades & finishes?

I use existing layouts to avoid pulling permits.

Just a lofty goal to get some advice on. i like all the intuition from the property history..

I'm not in love with the new layout but it was definitely the right decision to add another bedroom and create an open floor plan. 

Your intuition is right - we live in Stamford where prices (and taxes) are high and cash flow isn't the greatest :) We're looking within this area and neighboring cities.

Working on the layout now and would love some feedback.Here's the original layout of the property. 

@Mo FarrajHi Mo.It's a little counter-intuitive, but what I do is become an expert in only one locality.One would think that if you have a sufficiently large enough Portfolio, in my case the Assets would be worth around $20 Million, then you would diversify to reduce risk.BUT...It's already so difficult to follow all the different changes in neighborhoods, like new developments, Gentrification, zone laws, building codes, etc.Then Changes to Tax Laws.

Not a single one uses their intuition and street smarts to help select the best tenant?