I bit usual layout as its set back from the street with its own access lane and backs to a large apartment building and has taller wood fencing, but the owner has lived there for 12 years and is 73 now and tired of playing landlord with his neighbors/tenants - he has the usual tenant adventures going on right now, such as an eviction and probably isn't a thorough tenant screener. 

The 2nd floor layout was not condusive for such as the layoff is a bit boxy.

Schematic Design (new layout, demolition plan).  

.- the 220k includes upgrading a separate half bath to a full, completely moving a full bathroom (so layout isn't weird), demo'ing a shed, and then finally adding the expansion.

I think you nees to lay out the costs and then decide.Converting to gas depemds on how far you are from service now.

Hen you can adjust as needed to lay out the money portion of it.

Not just for doing to the work myself but recognizing what will work and what won't in certain layouts or situations.

Any help on how to better layout these old kitchenettes would be appreciated.

You can layout the cash for portions old construction and be reimbursed by the hard money loan.This should minimize the amount of cash in the deal and enable one long term mortgage at the end that takes all your cash back out.

A lot of the stock plans have horrible layouts and don't take into consideration your site conditions.