This is the big thing that a lot of people miss, your policy is what dictates on how repairs are paid (Replacement cost (RCV) vs. actual cash value (ACV)), and not necessarily your adjuster. 

Your financial and other situations should dictate which way you decide to go. 

., business letters, PowerPoint presentations, dictation, emailing, excel spreadsheets, research, marketing, advertising and much more depending on the experience and knowledge of that particular VA.

I love to see people from the Philly area joining (Almost everyday now it seems).I'm no expert but I'll try to tackle your questions as best as I can.1) I don't think the area should dictate your strategy or financing options.

your current position should not dictate your success.  

However there are many factors to think of that will dictate how you should "structure around that". 

And, which is more important - the relationship with the family member or the relationship with the boss (actually think about this - and don't fall into the trap of saying what social norms dictate)?

You could move out after a certain period of time (dictated by loan terms) and then have both as rentals.

But, I do feel like he is lying to me about doing the permit process in the backend, and instead of telling me that maybe he hasn't had time to even start the process, he has been lying to me this whole time about even starting the process, because I have NEVER heard of government employees bypassing the process dictated by the government, just to help someone out. 

The starting point is usually dictated by what you can afford, and less about what size you prefer.  8-10 lots per acre is fairly common.Properties within city limits of virtually all states usually have ordinances that have acreage, lot size, and setback requirements, among many other things - such as street construction standards.