The short version
These bands answer different questions. Whoop 5.0 is the proven, coaching-grade recovery platform for people who train on the daily Recovery score — and it charges a subscription for that. The Fitbit Air is the cheapest honest way into continuous HRV and sleep, with no subscription wall on the basics — and the open question of unvalidated accuracy.
When the Fitbit Air is the pick
You want a 24/7 HRV and sleep trend without paying a monthly fee to see it, $99 is the right budget, and you are tracking your own trend rather than chasing validated precision. As a first-generation device, judge it on your own multi-week trend, not its absolute numbers.
When Whoop 5.0 is the pick
Recovery and strain coaching actually changes your training, you want a mature, validated platform, and the ~$30/month is worth it for the model. Whoop is an instrument for people who act on the signal daily.
The honest note
Neither replaces active practice. A tracker — either of these — tells you how you recovered; it does not change your state. Pair whichever you buy with an active practice like HRV biofeedback, which is the part a band cannot do.