Handwritten on white paper, then scanned and printed onto yellow legal pad paper, writing in owner's name and property address, hand writing addresses (and return addresses) into pastel colored invitation envelopes.

My search has included analyzing the prices of homes in these markets, driving around the neighborhoods, checking on occupancy restrictions, student permits if required, college enrollments, crime statistics, etc.

Why restrict yourself to the Irvington area?

This thing is an off-market, 9720 ft2 mixed-use building that needs a lot of work (say, $300k purchase price and $200k reno, with 10k closing/legal/deed transfer costs). 

The Holton-Wise legal team managed to get the fine dropped a bit but I still had to pay it, plus legal fees.

A normal fence is usually required to back a few inches from the property line, if you had it surveyed and know exactly where that line is, then build it the required distance back, usually it's about 4", so give them the 4". let them challenge you, that's why i said a fast mason, have the wall built then fight them legally if they challenge, at that point it will be up. you have the proof of the property line, let them get there own survey to fight you.

I'm not asking for a legal opinion, but rather somebody who's been through the process before and their thoughts (and knows what to expect). 

do you have legal forms you make them sign?

If tenants rented the house part of that month (before the disaster), then I believe a prorated rent amount is legally due you.

I know i can legally just enter if i want to with proper notice but i dont want to ruffle more feathers.