Buying a relatively expensive watch does not come down so much to what you do rather where you assign value. There are people will easily purchase a Rolex for example on Credit and pay it off over time. They do it because they are enthusiasts and passionate about such things. I definitely do not consider myself especially well off other than to say I educated myself, work hard and I am at a point in my life where I have been able to purchase a New Omega and recently a used Rolex. I may not be so fortunate in years to come.
Your comment about not being able to stomach paying more than $1k is fair enough. My comment would be that I cannot stomach paying many more $Ks say for a new fancy car and ‘watch’ it lose 20% in value the moment the dealer hand you the keys and you drive out of the sales yard. In my opinion you should not fork out even half the amount you suggested if it is going to bother you and you end up with 'buyers curse'.
If you do want a a name brand watch and are thinking of going used becareful of being tempted by deals that are too good to be true. You will either lose or your money or end up with a fake. Do your research and be prudent. There a few known regular sellers on Timezone that are considered trustworthy.