I don't think it's the worst idea but I have a couple reasons I am actively avoiding getting Omicron this month:

• I expect a strong chance that a new variant displaces Omicron in the next say year (we had ~3 displacements in the last ~year: Alpha Delta Omicron). So then the question becomes, how much does Omicron protect against the next big variant (probably a good amount). Vs how much does your vaccine already protect you against the next big variant (probably similar). If that's the case, I don't see much advantage to getting Omicron.
• I'd expect Omicron to infect a large fraction of the population, but it's unlikely to infect "almost everyone" (before Omicron is displaced by the next big variant). So I definitely think it's still avoidable.
• Getting Omicron in January is the highest risk time due to strain on treatment capacity. Also Paxlovid is becoming more available. I think the risk of very bad outcomes will be much lower in March.
• If what you're optimizing for is protection from severe disease, vaccines already do really well.
• The severity of Omicron looks less because more of Omicron's cases are breakthrough infections, which are less severe. If you look at the severity in people of a given vaccination status, it's about ~50% less severe by the latest estimates I could find, which is a lot better than Delta but similar to Alpha.

I have a post on some of these topics: https://firstsigma.github.io/omicron

Within reason, I can see how it might be wise for you. I think the largest uncertainty this question hinges upon is whether hospitals in your area have the capacity to treat you if your case is unexpectedly bad. You can get a good sense of this by monitoring available ICU beds in the immediate/short term, but beyond a week it's hard to know.

And here's maybe a more important question, though far harder to model: will hospitals in my area have more/less capacity to treat me later, if I just catch it at the naturally occurring rate?

I'm in NSW, Australia, so even though Omicron is somewhat milder, I'm not inclined to catch it right now. All the hospitals within a reasonable range are getting full and making hard choices. So if I'm going to choose a time to ideally contract it, I'd have to shoot for just after the Omicron wave burns itself out. I'll get the Pfizer booster in February (after the initial 2x AZ mid-2021) but that's a month later than I was hoping to.

And thinking about hindsight counter-factuals on what I could have done differently is very confusing in different ways (yes, I agree hindsight counter-factuals are verboten as actual evidence). I should have booked in my booster before everyone else here realised Omicron was going to significantly change the situation, or that could have been a good time to inoculate by contracting it. Unfortunately, by the time I could possibly have had enough information to know it was a good idea, it was too late to beat the rush of cases. Not sure if that dynamic would have been in play where you live, but it fascinates me that 3-4 weeks is long enough to resolve a lot of the very salient things we didn't know. It may have resolved almost enough unknowns to be sure about when you'd want to catch it. But I'm not sure if we know when people in different locations should contract Covid intentionally. I think my inner jury is out, but I have the sense that I missed the best time I could have caught it.

I'm still worried about the risk of long COVID. See e.g., Katja Grace's recent post, though I am still trying to incorporate the comments on that post into my mental model. I also saw some really concerning Twitter threads on long COVID, but I don't know how good the posters' epistemics are, and don't know how they interface with say, Zvi/Scott/Elizabeth's earlier analyses of earlier studies on long COVID which treat it as a minor concern. 

If you have your booster then the symptoms of omicron will likely be mild. Anecdotally I just recovered from O after booster and my symptoms were so mild that if I hadn’t tested, I wouldn’t have known. My two unboosted friends suffered more with 3-5 days of flu-like symptoms. My decision was to get my booster, take hi-dose vitamin D and get on with my life, although everyone will have to make their own cost benefit analysis based on personal health situation, whether they can afford 5 (or 7 or 10 depending on country) days quarantine.

It seems to me that the best argument against this is that there are less harmful ways to obtain an additional inoculation benefit, through additional vaccination. Either by getting additional shots of Pfizer/Moderna beyond the third shot, or by getting RadVac in addition to Pfizer and Moderna. I would imagine that there is some very large number of Pfizer/Moderna/RadVac vaccinations shots that would have comparable negative effects on health as getting Omicron once (maybe 10 or 100?), and that getting this many vaccination shots would provide much more protection against covid than intentionally getting Omicron.

In the case of Pfizer/Moderna, in my understanding, I don't think it's too difficult to get more than 3 shots, as many vaccination sites do not ask about prior vaccine status. I remember reading a news story about a person who got dozens of covid vaccines in order to collect the government incentives for doing so.

I'm not currently planning to get a 4th mRNA shot in the next couple months (let along 10), but neither am I plan but neither am I planning to intentionally give myself Omicron.

I just had omicron while travelling in Canada for New Years and the biggest negative was being isolated during my vacation/ away from home. All 3 people in my group ended up getting separate hotels for two weeks, we probably spent 5k on hotels and cancelled flights and covid testing. Any enjoyment we hoped to get from the trip was ruined. Had to jump through lots of hoops to get back home too - returning via land border as by air requires 2 + weeks after a positive PCR (which I wasn’t able to get until a week into the illness, due to holidays).

I recommend going through effort not to get omicron while travelling, as the isolation is the most salient negative aspect. The disease itself was very mild after being boosted. And if you have upcoming travel plans, testing positive on pcr (which you might for weeks afterwards) is another big concern So if you are thinking of travelling in say March, it may be smart to get it now with your whole household (so you don’t need to quarantine from eachother). Be sure to document you had it with positive PCR - some places want either a fresh negative test or an old enough positive test, but look at the details of wherever you’re going