This portfolio consists of both my own properties held by my business as well as properties under our management owned by other entities and individuals.  

Found a local investor who was very eager to buy right on that very block.

When dealing with individual sellers, the most important thing is their motivation. 

I did it with H&R block for last year and didn't see what the saved number even was.My last mortgage was a real pain to get.

I am a tax accountant working at a big 4 accounting firm so a large chunk of my time is blocked off by tax busy seasons.

I have a chance to buy a property on East Upsal, 2 blocks from Germantown AV.

There is a tax form (W7) they need to complete to get them a ITIN (Individual Taxpayer Identification Number) for tax purposes since they don't have a SS #.......but that can be done after they invest and before tax returns are filed by the partnership.  

Also found a home there 4/2 2300 sf two blocks over in same neighborhood just sold for 480k.

Or are they typically sold individually?

As others have mentioned, learn the fundamentals and analyze each property individually.