Of course there's always that thought in the back of my head that I will get too used to it and give up my fairly frugal ways (I'm not nearly as hardcore as some here and never will be). Honestly I don't think I have any intention on living life the way I was in the past. Giving up your best years in order to save a few more dollars just doesn't seem worth it anymore - but maybe that's because I'm already in a fairly good spot.
Anyone else been through similar?
Yes. Like you, my midlife crisis came early though I was in my mid-30s rather than your spritely 28. Great job on being frugal, working hard, and investing - you should be proud of that. Very few people are anywhere near FI in their 20s.
I was consumed with school and career throughout my 20s. Fairly frugal through most of it (with a few slip ups along the way), very focused on getting to FI. This was good, no regrets. But by my mid-30s I realized life was passing me by. Your bolded quote above is a great summary of my thinking, very much in line with the following quote from the Dalai Lama when he was asked what surprises him most:
Man. Because he sacrifices his health in order to make money. Then he sacrifices money to recuperate his health. And then he is so anxious about the future that he does not enjoy the present; the result being that he does not live in the present or the future; he lives as if he is never going to die, and then dies having never really lived.
Pithy quotes like this are often used to justify consumerist culture, to discard all common sense and do and buy all the things. Which is unfortunate because it misses the point. IMO this is about having a greater awareness of what we do and why. Making money should be a means to an end, not an end in and of itself. Midlife crisis usually happens once you're relatively well established and enough life has passed that you realize you're not immortal, then thoughts turn to questions of what's the point, what am I really living for? Done well this can be a healthy and life-giving process. Done poorly, such as avoiding the discomfort by use of substances or buying sports cars or other means of trying to recapture youth, it can result in disintegration.
All this to say: Take the road trip. A couple months on the road with a motorcycle is not going to break the bank, especially if you keep the accommodations cheap. But I would be mindful of the process - what do you hope to get out of it, what do you consider a good life and why? Travel is a great catalyst for such questions because it breaks us out of the day to day. You may discover that you want to do more travel at this juncture in life, or you may find that you want to deepen relationships with friends and/or family, or maybe volunteer more, or get in shape, there are many possible combinations.
California has many beautiful areas. Traffic can be an issue, but can also be avoided with some planning. Two tips: 1) Don't visit touristy areas (Yosemite, Big Sur, Tahoe) in the peak season and especially avoid holiday weekends and 2) avoid the Bay Area and the greater LA area. Touring the Central Coast from Monterey/Carmel, through Big Sur, and down to Santa Barbara in the Fall (after Labor Day) would be a fantastic experience. Way less busy, and that time of year typically has the best weather along the coast (warmer, less fog). The Fall is also a good time for the hwy 395 corridor along the Eastern Sierras, or the Lost Coast.
