Matt;

Good for you for knowing what you want and asking for help. I hope others will chime in with their thoughts. In the meantime I will get the conversation started.

You have the benefit of age and wisdom and more circumspection and are wise to seek to make the learning curve as steep as possible. If you’ve read our book(s) or spent anytime on this site you already understand that that your fitness plays a big role in afely enjoying the mountains. So, I won’t beat that horse to death; only saying that Training for the New Alpinism should be on your reading list. From it you can build your own training plan. We also sell training plans for those who want to have the plan laid out for them. The one I would recommend is the 24 week Expeditionary plan as it most closely follows the book. Fitness is not all there is though. Even with modest mountaineering goals you will need to develop a set of skills that have no relation to any other sports activity you have participated in. There is only one way and one place to acquire those skills. That is by learning and practicing in mountain terrain. I would suggest acquiring a copy of Freedom of the Hills as it provides the broadest brush look at the full spectrum of mountaineering skills.

After familiarizing yourself with the concepts in these two books you will need to find friends with similar interests whom you can learn with (the slow route to competence), join a mountaineering club that offers skills classes (slightly faster route but fraught with its own problems), or hire a professional guide to teach you these skills (expensive but definitely the fastest way).

I hope this helps get the wheels turning. Welcome to the fold.

Scott

Matt,

Buy the book and start training. Marathons and Ironman will give you a huge head start, but you need to begin the sport specific training.
IMO, you would be wise to purchase the training plan instead of DIYing. Very short money for what you get.
Plan a trip to the White Mountains of NH or CO or the Cascades or anywhere you and maybe your family want to go in the Alps or the lower 48 with mountains. Hire a guide for a long day in which you prioritize learning over the summit. Make it explicitly clear to both the guide and the owner of the guide service that you are there to learn, not be towed up a route. Having the guide work with you on rope systems and protection will be incredibly helpful. Especially if you can’t find a local community.
Try to find a local community. Join a rock gym and climb twice a week if possible. Find somebody who climbs trad and learn the knots and rapping from them. You need a lot of knowledge covered in Freedom of the Hills but it’s best to have a human explain it. Rock gyms aren’t a substitute for alpine terrain but you will learn how to belay, how to tie-in, the figure-8 knot, the benefits and weaknesses of belay plates vs. grigris, etc. You’ll also become accustomed to being lowered and to hanging off the ground (skills best learned indoors, imo).
Time in the mountains is the best way, but, you can buy knowledge and experience via a guide. Wisdom and judgment will not come from your wallet, however. Good luck.