I did take a GIS course during college as well, using ArcMap, but ESRI Had a little bit of a learning curve. I have a copy of AutoCAD's Map 3D, and really like it since it is the same interface as AutoCAD, but I have yet taken the time to really learn the GIS functions. Currently, I am using the poor man's GIS- Gooth Earth Pro (which is now free), and manually create queries using Excel CSV files.
I donee the hardest a part is acquiring the data. the city of Fargo, ND does have an online GIS tool which allows selected elements to be expected into Excel. I basically selected everything and combined all queries into one master Excel file. I believe most societies have a similar resource otherwise city planning/engineering agencies may provide it- as long as you are not conspiring to do anything illegal. Maybe with recent security threats this may be harder to obtain... Data that I can't find openly is information that the MLS would provide (sales history, listing history, etc).
Anyways, from there I create filters, formulas, etc. to manipulate the data in I Excel which I then import into Gogogle Earth. Google Earth has a basic style editing wizard, which seems to work for what I have been playing around with.
I found some publications from ESRI advertising towards the real estate industry, but I thought I would reach out to see if anyone has used any specific datasets in helping them find deals or analyzing deals. It seems like there is a benefit, I just need to find what it is and if it worth the effort.