And sorry for the thesis term paper of an explaination.

Does anyone have a recommendation for a software to create a layout/drawing for my contractor to use for his permit request?

They're better off if the apartment doesn't sell, actually, as they have to change billing records, etc... just more work for them, with no benefit -other than absurd "application" and "processing" fees (often totaling more than $1,000) that the clerks pushing (or sitting on) the papers rarely see.I've bought and sold in many other places, but trust us when we say, it's really different here.  

I have been a landlord since 1982 and I have also flipped a fair numbers of homes over the years.A couple of years ago I discovered the "paper" side of the real estate investment world.

I am currently converting paper assets into hard assets (SFR's) for the long term investment as well as building passive cash-flow to exit my current career.Currently we are buying houses off the MLS as well as distressed properties (estate sale/pre-foreclosures) that fit our investment criteria. 

Assuming that's the case, does he meet with an architect first to get ideas on paper?  

You could even lay out some purlins and install real metal roofing.

I send out between 5k-7k letters a month..I have a bulk mailing permit from USPS..So it cost me roughly $300 per 1000 letters mailed...I print my own letters ( not yellow letters) I use simple white copy paper.

I will be printing the letters myself and have the font looking real good on yellow lined paper.

I get my pen and paper and mentally get ready.