Rehab, permitting, and plans

[Curt Bixel]

I am a long term landlord and have substantial experience as a handyman.  I am fairly new to buying a beat up property, rehabbing it, and then keeping it for a long term rental.  I recently finished my first rehab, and learned quite a bit.

I have my eye on another property, and am looking for some input regarding planning and permitting. 

The property has a strange layout.  Here is a basic diagram. 

Currently, both reasonable entrances to the building take you through a bedroom before you reach either the living room or the kitchen.  That is not a great layout.  You can see a boarded up door on the south wall of the kitchen.  (South is down in the diagram.)  It seems likely that that used to be the main entrance before an alley was constructed that ran so close to the home that the door was no longer usable.  The alley runs within 3 feet of the south wall of the building. 

The property is also quite small, so running a hallway along the south part of the large bedroom and using the front porch as the front door makes the bedroom at the left side of the property too small to be usable. 

What would make the most sense to me is to simply create a new door on the north side of the living room or the kitchen and use that as a main entrance.  This sounds like it would require permitting if I were to do things right.

If I purchase this property, my plan would be to pull permits for everything and plan on doing it right.  This would involve replacing all windows and at the same time adding a new door to the north side of the kitchen or living room and building a small covered porch for access.  Then having the property completely rewired, as it is mostly knob and tube.  I would get the HVAC done and have the plumbing replaces, as much of it is the CPVC stuff that is supposed to be unreliable. 

With a full kitchen and bath remodel, the project would pretty much result in a fully rehabbed property, as the walls, floors and roof are in good condition.

What I don't know, however, is what the planning and permitting process would look like for this, and it would be good to have some guidance.  I really doubt that the plan I shared above is anywhere near detailed enough to share with anyone who would sign off on it. 

Any thoughts?