About 4 years ago, I bought a Tissot Le Locle with a white dial and black leather strap. I was in love with that dial and this was my first "expensive" watch around the 500 euro mark. Before that I had Casios until I was ~22 then Swatches and in 2008 I bought a Swiss Military Hanowa chronograph which was too expensive for my budget then (around 300 euros) but became my daily beater for almost a decade and it still operates well (apart from the inability to source any more the original strap and have it on a black fabric one).
And then something changed. The Tissot got me in a brave new world. Moreover, it was a dress watch, I could not wear it on a daily basis (I do not wear suits to work). I started a fund for an "expensive" watch again, this time targeting between 2000 and 4000 euros. But what to get? Can internet searches and a couple of minutes wearing it in a store be enough for such a big cost? And then I came across cheap chinese mechanicals. I thought why not buy homages of the watches I liked to see how they grew on me, like a try before you buy period. And to begin with, I was considering watches like the Tevise T801 around the 20 euro mark, which was actually the first I bought.
At least that was what I had in mind initially. The reality is that I got 11 watches just the past year. Only 5 of these could fall in the category of "checking whether I like it enough to buy the expensive one". The rest were watches I simply like and I would never pay more to get. For example I always liked flieger watches, but I would never wear one everyday. I got a nice Parnis one. I wear it occasionally and I really like to see it. For ~50 euros I paid, it is simply great, I would never spend more. Or on the other hand a watch like the AP Royal Oak. I will never be able to buy one (and even if I am able to buy one, I will spend the money elsewhere) - the Didun is just perfect.
Of course, very soon I learned that you cannot get a descent mechanical watch for 20 euros. You need to spend more than 50 to get a descent working movement, sapphire glass, nice straps, all stainless steel cases.
One year down the road, I have spent 500 euros for these 11 watches and I enjoy every euro I spent (ok a couple of watches were not that good :) ). Will I buy more? I have at least 2 in my waiting list, but to be honest I think I will spend more time enjoying the ones I already got. Will I buy an expensive one (2k-5k)? Probably at some point in the future, but it will be with air miles covering most of the cost and not hard cash.
I have also started enjoying learning more about maintaining my watches myself. I fixed a broken stem, I changed a crystal and I have a movement in the post coming to exchange a broken one (a quartz miyota OS90 in a Festina which was a gift and enjoyed it for 1 week only before it fell on the floor and the movement failed).
And do I have a grail? Yes, but it is something I could get even today, if only I could find one. Back in 2006 I fell in love with a Tag Heuer Link, which at the time had a dial I really loved (WJF2110).