Good luck on your set! A collection of 1795 coins is a very advanced undertaking, and I wish you luck!
To answer your questions:
1. First, the die clashing does not automatically make this O-116, but a clash in this area is seen on the O-116. Clashes can appear on numerous marriages, and a reverse could be paired with a difference obverse (and thus be a different marriage). The identifiers for the O-116 can be found here: http://maibockaddict.com/1795-o-116-r4
2. There are two primary references for early half dollar die marriages. The first is Overton's "Early Half Dollar Die Varieties" and the second is Tompkins "Early United States Half Dollars." Overton covers the entire series from 1794 to 1836 in a single volume, and has been the standard reference for decades (updated periodically). Tompkins is a new work, in the last few years, and is coming out in 3 volumes. Only the first volume is out, covering 1794-1807. It is gaining acceptance, but is nowhere near as widely recognized yet.
So, to go back and finish answering part 1 - "O-116" is the numbering from the Overton reference, T-11 is the equivalent from the Tompkins reference. 2/2 indicates the die state, with 1/2 not having the clash, 2/2 having the clash.
3. Properly graded coins will cross. You need to choose properly graded coins, coins with good eye appeal, and original coins - and then you will have no trouble crossing at all.
4. Small rim nicks are completely acceptable on old coins like this. I'd avoid an AU coin with a decent nick, but I don't mind a small nick like this on an EF coin.