Help me decide if a vintage Constellation is right for me

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Unpopular opinion: for a newbie, I'd still recommend Omega Enthusiast for peace of mind (even after doing due diligence).

Have there been questionable watches he has sold? Probably (like most reputable vintage dealers). There is nothing 100% risk-proof in life. But, of the hundreds of watches he's sold (thousands now?), bet the vast majority have been 100% fine and original. If a problem were to arise (regarding a fake watch), I'm certain he would fix that since his reputation and business is on the line (doubt he would risk that).

Yes, his prices are high; but god forbid he can make a profit since it probably is his main income (YouTube streaming probably is not much). One must also factor servicing costs (unfortunately there are many butcher watchmakers out there who can completely ruin a watch) which he clearly has competence and a passion for. Have not heard any complaints on his servicing or warranty he provides.
 
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I'm not going to criticize a dealer for making a profit, but the particular dealer being mentioned in this thread has prices that I consider to be offensive. I think that he must cater to naive buyers who feel that by spending as much as possible, they can ensure that they have purchased a high quality and authentic item. And maybe if you have a high budget, are only going to buy one watch and you plan to keep it forever, it doesn't matter if you burn an extra $1k-$2k. However, for those that don't want to waste money, or don't appreciate being exploited, there are any number of ways to get watches that are as good or better for 1/3 to 1/2 the price. Personally, I'm not going to recommend that seller.