Why have more of our generation not joined the VFW?

Originally because I didn't qualify. When they opened up Kosovo as a qualifying conflict to join I was offered by my Post back in my hometown and signed up. Unfortunately I've moved around a lot so regular participation has been problematic. But I am now a life member and plan to look into a local post when I settle enough to participate.
I do know for a large part that it's perception. Most see the VFW, and in a lot of cases the Legion (although the motorcycle association sometimes helps them), as older retirees from anywhere ranging WWII to the Vietnam War. They see it as a guy's military club to sit around a bar in the club to smoke, drink, and harumph about the old days or reminisce about the women in their travels. And in a lot of cases it isn't far off. The VFW needs to start re-aligning to keep those old schoolers while also attracting the newer types ranging from activities to intra-group interaction. Bring in a coffee bar with the booze, restrict the smoking to outside, install reliable free WiFi to members and possibly add a couple of computers in a café of sorts. Keep up the lobbying for traditional supported positions but start looking at possible newer ones as well that the younger generation(s) see as being important.
The VFW is one of those things, from what I've seen so far, that might be it's own worst enemy. It cannot stay entirely the same and expect to survive. If it can prove the ability to adapt, and with the much larger pool of recruits now with Desert Storm through Enduring Freedom, it has a chance to endure. Overall it is a great organization and I know the guys in the Post back home do a lot with the local schools and such. But it's usually the elementary schools for plays and the like. I don't recall seeing them a lot around the high schools, recruiting centers, or separation/transition briefs on bases.

I joined the VFW but living here in Denmark the only thing I get is a magazine a few times a year. I do enjoy it. I guess I joined because I wanted some type of a connection I guess.

After reading many of the posts and replies here. I feel that these VSOs are VW Bug drivers in a Corvette race. To date I have been an off and on member of the VFW and the Legion, because the status quo has not changed for any of the local chapters. I am not interested in drinking in a dingy bar , eating bar food or have my dues support the bar. Also I am not covered in TATS, have a pony tail or ride a Harley, so I don't fit in there. The old timers (Lord Bless Them) are rooted in their past and refuse to change.

We get engaged while on Active Duty by the USO, Navy/Marine Corps Relief, CFC, MWR and then also belong to Command organizations (CPO/NCO, etc.). The reason why more of us don't join VSO's is because we don't have any direct connection with them, unless the post nearest one of the stateside bases reaches out during the short time we're assigned there.
The other problem is that screwed up admin/service records is the norm, and the stupid way the DoD went about approving and awarding the OIF medal and CARs early on disenfranchised a lot of people. Hell, I took all sorts of incoming indirect fire, but because I wasn't afforded the opportunity to shoot back at those cowards, I don't get a CAR? I guess I shouldn't have ducked so maybe I could have gotten a Purple Heart, hmm? I had to *trade* my GWOTEM to get the ICM, and was also awarded a JCOM by the Army but then the Navy has some stupid protracted process for submitting all this before it "counts"? Yeah, meanwhile, I've got my REAL job to do, and since I didn't do the job for the awards, getting paper-pushers to do their job and fix all the paperwork remained a low priority. Well guess what, it's FINALLY all on my DD214 now, but this is the reality: At the end of the day, everything is on the individual (and your retirement clerk, LOL). If somebody wants to give me a break because I served, it's the exception, not the norm. It was nice to walk into a USO on the rare occasions my flight happened to be in the same terminal, but now I don't intend to set foot in one of our Nazi airports ever again. I've come home to a country that is more like the USSR than when I joined. I don't feel entitled nor obligated and won't behave as though I am. It was a job and I did my job. I did a lot of stuff for a lot of other people and I never expected it to come back around; if it does, great, but I'm not holding my breath or trolling in VSO's trying to get a free lunch. Wife and I belong to the local HOG chapter because we get more out of a riding organization than a drinking organization, and when you ride, it doesn't matter that the meetup is over 30 miles away.

I joined the VFW just over a year ago. The first person I met when I walked through the door was a guy who walked off a landing craft onto Utah Beach on "D+4".

My active duty time doesn't qualify me for the VFW, or the Legion. There might be a loophole that would qualify me based on my civilian experience (Berlin Brigade, West Berlin), but frankly it doesn't seem to be worth the effort. Yes, I know that these organizations do serve the community, but the perception is more that they just gather in their hall/clubhouse/whatever and drink beer and play pool. I've never seen any compelling need for me to make the effort to try to join, and no one has ever made much of an effort to recruit me.

I am a life time member of VFW post 1435 but I have only been in the hall 3-4 times. As one of the other guys said I know my dues go to help other veterans with scholarships, help with emergency bill pay, and other things. But after being stationed in S Korea and then England I am burnt out on the whole bar seen. And I know the main reason most of my friends don't join is because they thing that all it is, is a good old boys bar. I think the best thing the VFW could do is have every post on social media and do more in the public and let people know there is more to the VFW then just a bar.

As for your question about what do I do to continue to serve I am a veterans outreach coordinator for Vet Corps. While technically an Americacorps member I am paid by the Washington State Department of Veterans Affairs. I connect student veterans and their families to local, state, and federal resources.

Some feel that serving the country is payment enough and think the "dues" is a load of B.S.

I think its outdated and perhaps a new not for profit could be in order to serve todays veterans. entrepreneurial idea for free. now do something

the one thing I did forget is...if you served in the Military but did not serve in Combat...you can still join the American Legion...which is a Veterans Organization.