Just turned 40 and I’m in my second year of cycling.
Picked up my second knee injury in 3 months a few days ago. Totally unrelated to the previous injury and I’m 90% sure it’s an over-use type issue. I was at the end of the final hard week of my first ever medium volume plan (ssb1) when the pain came on and knocked me on my ass. On the bright side this is now supposed to be my recovery week anyway so I won’t feel like I’ve lost much fitness staying off the bike completely to rest my knee.
Here’s a brief history of my more serious sports injuries that I can remember:
Started playing basketball competetivly from age 14. Around the age of 17 my first knee problems started and I would play through the pain for a further 10 or so years before I had to move on.
Went from Balling to Lifting for the next decade and proceeded to procure a whole bundle of niggling injuries pushing myself too far. Most notable of which a myriad of back and shoulder injuries but I stuck to my m.o. and trained through it most of the time.
My worst injury was a herniated disc in my lower back. It took me 4 years to get over, during which of course I kept weight training like the idiotic, addicted masochist I clearly am. 
In the summer of 2018 I was finally beaten after a lifetime’s worth of fighting through (and making things worse) and I had to, for the first time ever, cease and desist all weight lifting activities. No easing off - just 100% couch potato. A month later I was hit by my one and only bout of clinical depression, needing medication to get through it before I took up cycling and the rest is history! 
Anyway, as I hit the ice packs and ibuprofen for what feels like the thousandth time in my adult life its got me wondering how many kindred spirits are out there who have had the same kinda lifetime of sporting related issues that I have bounced through and kept coming back from in spite of their bodies continual failings? 
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I would say that given your history you need to fundamentally change your approach. Learn to listen to your body and dial things back and get treatment when it’s a minor niggle rather than pushing through the pain until it’s a major injury. See a good physio who works with cyclists and also a good bike fitter who understands physiology (if you can find 2 of the above who already work together that’s best of all), between them they’ll make sure your position is decent and identify any strength or flexibility limiters that you need to work on. You need to work with them to figure out a maintenance routine off the bike that enables you to train hard on it without injuring yourself.
I have a less extreme version of your history. More from running than cycling, but I’ve had my fair share of cycling overuse injuries as well, plus various crashes on both bike and skis. Prevention is far better than rehabilitation. My garage looks like a Decathlon store with all the things I’ve tried to keep me healthy - Swiss ball, bosu ball, wobble board, various massage sticks, and a whole assortment of bands, spiky balls and foam rollers.
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I both feel your pain and agree with @cartsman .
I just turned 39 and feel like I’m just playing wack-a-mole with one issue after another. At this point my “maintenance” activities for managing my potential injuries take almost as much time as my work-outs, but they keep me going. Knees, back, hips, nerve stuff, muscle tears, joint pain, yadda yadda.
I think the best thing we can do (and I fail at this a lot) is just to accept the situation as quickly as possible, and do the right thing for your body despite what you want to accomplish training wise. For example, a couple months ago I was running and stepped funny and injured my SI joint. Trying to “HTFU” I ran another 3 miles on the injured joint. If I had just stopped when I did it, I probably would’ve been fine in a few days, but instead I was limping around like an old man for a month. Conversely I had a moderate muscle pull in my quad last week, took a few days off, and decided to start my recovery week a week early, and I think I’ll be back on track later this week.
This lesson is definitely easier said than done. In my head (and in my maturity) I’m still in my 20s, but sadly my body has it’s own opinions.
Keep your head up, be as adaptable as you can, don’t be afraid to get some help from bike fitters, personal trainers,etc, and see your down times as an opportunity to take care of the stuff you’re putting off when you’re training :). There are bad-ass 70-somethings at all the epic rides I did this year, so obviously we aren’t out of the game yet, we just have to play it smarter.
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I think I’m in the process of chasing injuries around my body. I’ve a long history of knee problems dating back to my early 20s (I keep a list and my right knee is up to 9 separate instances of injury!), but I also seem to pick up ridiculous ones. About 18 months ago I tore a ligament in my foot kicking a ball around with my daughter, and since that healed I think I’ve given myself a hip/abdominal injury as a result of the compensation!
As well as getting early treatment for specific issues, it’s also worth trying to find underlying causes - I thought my hip was fixed earlier this year, but it’s come back - presumably because the cause is still there. I think I need to make sure my foot and shoe are good and hopefully that will stop the hip from recurring again.
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@cartsman mentioned all the important points. It doesn’t make you strong if you can push through pain, the body is sending signals for a reason. Address problems very early. If you get tendonitis (e. g. in the knee or the achilles tendon), address that immediately. There are some easy exercises and you may have to stop exercising. Consult a doctor or a physiotherapist who are familiar with endurance sports. Also bike fit refinements can help.
In my case (I’m 38, rapidly approaching 39 with two knee surgeries), that meant using pedals and cleats with (way) more float (Crankbrothers pedals), even though mechanically my Shimano were still in great shape. I get sick more easily thanks to a toddler (she is the cutest germ factory you have ever seen), and I am more sensitive while I am sick. I’ve had my third bike fit recently since getting a road bike, and I am getting that dialed in better and better (got new handlebars last week and went back to the original stem).
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