While considering my response to X-wing 2e, I've been thinking about my experience with other games I've been involved with that have switched editions. These experiences have really impacted my view of 2e.
I had been playing Warhammer 40k for about two years when it switched to 6e. I wasn't heavily invested in the game. I was really only playing 40k because it was the game of choice for my playgroup. The change to 6e wasn't a big deal, since I could get a second hand copy of the rules from the new starter for about $20. ( The fancy $70 rulebook was rediculous.) However, a year later a new codex came out for my army that was significantly more than the revious codex. My army was small enough that I wanted to put that money towards building my army. My play group had started playing another game I was more interested in, so I sold off my Warhammer army in favor of the new game.
My other experience was with Heroclix. While they have never officially gone to another addition, they realistically did it twice, most recently about a year ago. Both times, all older figures were 100% compatible with the new edition. The first time changes were made, it became very evident that while technically the older figures were compatible, the newer figures were far superior so older figures never saw play (much like X-wing 1e now). Since Heroclix already had a retirement system, iconic figures were frequently redesigned in newer sets, and I primarily played competitively, this didn't bother me. With the more recent change, however, I was strictly playing casually and really only collecting. My son had never shown interest in the game but loved X-wing, so when they recently redid the rules, I dropped the game in favor of X-wing.
TL;DR
My 40k experience taught me that games will change and it will cost to continue to play. New editions were inevitable, but it was my choice to continue to play.
Heroclix taught me that smaller changes rendered older stuff obsolete. I could either buy into the new edition that made my current collection playable (40k model) or end up buying the new stuff and never use my old stuff (Heroclix).
In both instances, it comes down to my play group and size of my collection. Since I mostly play X-wing at home, I want to continue to play. Since my collection is small enough that one of each conversion kit will cover it, switching for me is reasonable. If my collection was larger or this was my first experience with new editions, I would probably stop buying X-wing and continue to play with what I have.