Don't discount the cheaper watches, they can be a good way of seeing if you actually like a watch or not, so saving on a chunk of change... For example, from the photos, I thought I would really like the Vacheron Constantin Overseas, but when it arrived, I couldn't stand to wear it. Sure, it looked fantastic, and there was nothing actually wrong with it, but everytime I put it on, a little voice yelled getitoffGETITOFFGETITOFF!!! I was glad that I'd only bought a cheaper, rather than more expensive version, and the only difference, was the movement...
Welcome to the party
[Edit to add]
Another example would be the Rolex 1655. Absolutely iconic watch, and one I thought I'd really like. While I can wear it without the getitoffGETITOFFGETITOFF!!! going off in my head, I don't feel particularly connected to it as a watch (despite reluming the dial and tinting the GMT hand myself) and although I think I will keep it 'as a spare', I don't think it will ever be my first choice to wear if I have an alternative... Not cash I regret spending, as it was incredibly cheap, in fact, I'm glad I only bought the cheap version, as had I coughed up $200+ for it, I would have been really frustrated, and probably re-sold it to try and recoup some of the loss...