Then a Civil Engineer, an Appraiser to determine what having a four unit would be worth, then a loan using the evaluation.

I've had some blue collar ones all the way up to software engineers and everything in between. 

First - I think your accountant should be providing you recommendations for cost segregation companies.It it most likely, if he/she works with real estate investors, that he/she would have a couple to recommend.Second - There are two types of cost segregation studies.Type 1 - Conducted by an engineering firm where an engineer will inspect the property.

Yesterday I was talking to and architect and engineer who is owed money.  

I've worked with a client in a very similar situation, and have spoken to many inspectors/engineers/builders, etc about things like this.

At time of purchase I had a couple of engineers over to look at a couple of things.

For foreclosures, you reverse engineer.

.- My Resources / Constraints: I'm in a by no means unique, but perhaps less common situation for those getting started; I'm a somewhat senior software engineer at a tech megacorp and should be able to save a couple of down payments per year for lower priced houses (100-200 in my area), or perhaps one medium priced house (300-500).

Reverse engineering. 

I would bring in a drafter or architect to assess it and see if you only need the building plans and pay permits: Building plans about $3k to $4k since everything is done... and city permits about $4k to $7k and make sure that you don't have to do anything major... front foundation could easily be $5k or more plus engineering work and stamp. : so, assess all systems and see for obvious things like : garage door, ceiling height, perimeter foundation and drainage, framing if you can, attic space, electrical, plumbing etc 4.