Specialize at the top from day one, or earn my way up

Your 424 number is too generous. A good share of those sides are dual agency or the same team on both ends, and some fraction never hits the MLS at all, so the sides you counted from public records undercount the off-market activity and overcount what's actually available to a new agent. I'd try to get the top five teams' actual side counts from their own marketing and subtract, then look at how many of the remaining sides went to agents with fewer than five years in. That last number is the one that answers your question.

pike's point about agents under five years is the one I'd chase too. If the answer is three out of 259, you have your answer and it isn't the one you want.

I hit a version of this ceiling on the investing side and the honest mechanism was that price band moves with who you already know, and who you know moves slowly. Five years is not an unreasonable timeline to go from nothing to a real presence in a high-end market, but you need income the whole way through, and general volume is how most people fund it. That's an argument for doing both rather than choosing.

The concentration you measured is the actual feature of the niche. High-end inventory and high-end buyers move through relationships and reputation, often off-market, and that access is difficult to replicate. It's what insulates luxury specialists from the general agent oversupply that makes your 9,000-sale market so brutal. The same thing that makes the top of your county hard to enter is what makes it defensible once you're in.

On the dollars, a 2% side on a $3.9M sale is $78,000. In the general band, a 2.5% side on $410k is $10,250. You need roughly eight general sides to match one luxury side before splits. That ratio is why a modest volume of luxury deals can support a business, and it's also why so many agents try, which produces the crowding you found outside the top five teams.

Two things bear watching if you commit. Buyer-agent commissions at the luxury level ticked slightly lower after the new commission rules, while the more affordable end held or rose, so the percentage pressure is marginally worse at the top. The absolute dollars stay large enough that the impact is cushioned. And the whole niche tracks the health of the high-end market, which is more cyclical than the median-price market underneath it.

The assumption your plan rests on is that access can be built rather than inherited. Test it with pike's number. If new entrants are taking a meaningful share of the 259 sides outside the top teams, effort is buying access in your market. If they aren't, the junior seat is the entry, and you're paying for the introduction rather than the split.

Nobody's costed the two years yet. Marketing at that price band is not the same product. Professional photography, video, print that doesn't look cheap, and the expectation you show up prepared. I'd want a real annual number before comparing paths, because $30k a year of spend changes which side of this is even affordable.

Luxury is relative to the market, which people forget. In my area the top of the market is $650k and there are maybe nine agents who get those listings, and it functions exactly the way windlass describes, same gatekeeping, smaller checks. If the access problem is what you actually want to solve, you can solve it in a cheaper market for a lot less money and then decide whether to move it.

hollow that's the most useful reframe in the thread for me. windlass, the question I'd ask myself is whether you like the work or the number. High-touch service to wealthy clients is a specific job with specific demands on your time and your patience, and if you'd resent it, the $78,000 side won't fix that.

One paperwork thing since you're deciding on a seat. Read whatever the team hands you for how the buyer representation agreement gets negotiated at that level, and who owns the compensation conversation with the seller side. Post-settlement the buyer's fee is an explicit negotiation on every deal, and at the top end the clients understand negotiation better than you will for a while. If the team's process is that the lead handles all of it and you never sit in, you are not learning the part that has value. Ask to see a signed one with the numbers redacted.