@Tyler Warne, you bet!

Direct mail and finding good wholesalers are your best bet for the best deals on off market properties.  

He has a good mix of Single Family and Multi Family.My question is what is the bet way to approach him about buying a majority of his properties rather than the few he has on MLS?

The biggest point I got out of the movie is that there is always someone betting against all odds.

Next, licensing for door to door solicitations, I bet you have that covered.Now, real estate license issues, how you pay can make a difference.

As for identifying real estate currently vested in names of two or more owners with a life estate and a remainderman (the legal term for the other interest), I'll bet there aren't that many of them.

Also his email is @gmail and his attorney is @outlook which is also odd to me as it doesn't incorporate their company name.

I think if you get a license before you start buying investment properties... your odds of buying property for yourself will significantly decrease.  

(This is also based on my experience at the end of 2015, I haven't been in 2016 yet).Sorry don't have much more to add, but I'd bet that others on BP have actually purchased properties there.

You could respond to ads, do online search, use the reference sites, including advo and the local Bar Association, however this may still not get you to a suitable practitioner.I'll bet there will be noticing issues, perhaps litigation.