Am I setting myself up for failure?

My .02 and I am no expert and someone else will probably give you better advice... I feel like you're overdoing it a little. If I am reading it right every day you are riding the bike for 40 mins twice a day, then adding in a Pump or HIIT vid, then 3X a week doing weights?

So on your weight days you are doing weights, then riding your bike to work for 40 mins, then riding home for 40 mins then doing a pump or hiit class? That seems pretty excessive for those particular days. I would say you are not allowing your body time to recover properly and will probably lead to exhaustion and maybe injury. But perhaps I am just reading it wrong.

In the end listening to your body is key like you said. I have def done quite a few double workout days like weights in the morning, T25 at night type thing. And I think it's perfectly fine if done frequently but not everyday. Again just my .02

How much of a change is this, i.e., how much is the recent add-on? If you added all the gym stuff (weights, classes, maybe more) all at once, it might be a little overwhelming - as much the time commitment as the workout load. But if you've been adding gradually, and are feeling fine, and (as you said) back it off a little if you feel fatigued, you're probably OK.

Listen to your body, know the symptoms of overtraining so you can look out for them, but beyond that, don't let other people (or your own *irrational* fears) stop you from finding out what you're capable of. (Rational fears and sensible caution are a whole different thing!)

In my personal experience, a lot depends on building up to increased activity levels over time. It used to be a big deal for me to do more than one workout in a day (spin class plus an hour or so rowing, for example). But after I'd been doing the activities for a while (or similar ones), it wasn't really a problem to stack more than one in a day, or do one of my regular activities for an extra long time.

If I add in something quite unaccustomed - like now I'm adding back in weight training after not doing it for several years - then I have to build it in a little gradually. However, I'm 60 years old, and my stamina really hasn't been the same since chemotherapy 15 years ago, so younger, more robust folks probably don't have to go quite as slowly.

measure distance NOT time... I can ride for 20 minutes and go 5 miles... OR I can ride for 20 minutes and go 10 miles... measure your effort not the time you spend exercising. ANY repetitive motion can lead to a repetitive motion injury over time, unless you apply some stretching and flexibility to your routine... diet can and will also play a greater part the older you/we get... THE GREAT news is you are in motion... keep at it.. even if you hurt, pull, strain, or sprain something, the fact that you ARE active will lead to a quicker recovery... do what you enjoy... have fun... everyone develops an injury at some point... JUST don't run with scissors in your hand

Prolly fine, then, what with the build up & it not all being new, as long as it's sustainable for you not just physically but also psychologically and time-budget-wise.

Keep an eye on the DOMS (as if you could ignore it ), though. Should stop being a big issue after a small number of sessions, IMO . . . if it doesn't, maybe back it down just a little in terms of reps, sets, weight or sessions/week - especially if it starts turning into fatigue. (I've dropped from 3 to 2 weight sessions/week starting back up because 3 was too fatiguing in deficit - just didn't feel like muscle repair was happening as it needed to . . . but like I said, I'm old.)

Foam rolling after the session may help if it's "just" DOMS, or a relaxing hot shower/bath and light stretch later. Oh, and eat enough protein, especially if you're in calorie deficit.

Maybe you can come up with some alternate active pursuits when you're home for the holiday, just to keep up a habit?