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Thanks all for the answers!
I thought about trying to respond to each individual but felt like I might end up repeating myself.
I tried to make this clear in my rather lengthy exposition, but perhaps was too muddled in my writing: I am totally aware that neither of these hats are top end. As I mentioned, I am excited to try the custom route, but since I have an immediate need, I need to make do with a compromise hat for the time being. A vintage hat would be an exciting find, but without having much experience with a fur felt hat at all it seems hard to judge the value/quality of something 50-90 years old that you can't see before buying. As you all have said, high quality hats at reasonable prices is sort of a thing of the past, but I can't help but feel that at around $200 you should be able to get something that is serviceable. To me that means something that looks good, feels good, and won't fall apart in a few years or after being exposed to the elements.
I don't think it's snobbery to say that there is a hierarchy of hat manufacture, in that you should generally stay away from sizes that are listed as S/M/L etc, wool is at the bottom, then wool felt, then fur felt, with rabbit being generally the lower level fur hat and beaver being better (and some other interesting furs thrown in occasionally such as nutria and the like). Custom is better than RTW, and there are differing levels for both.
But I feel like as someone reading a bunch of threads and stickies on this forum there doesn't seem to be much information in the way of what makes something quality vs not, beyond saying you just don't like a hat or hat manufacturer and bemoaning the fact that current production hats aren't up to snuff of vintage hats. It seems reasonable to me that if people are scared off of buying current production hats at a more entry/mid level than the more reputable hat makers will have no reason to offer them anymore and you'll either have the cheapo Chinese products or high end bespoke.
I think my fear over the Selentino is that it is not as widely sold as Stetson and there's very little information about the brand, and then when I read a bunch of negative things about them from Deadlyhandsome it made me worried that I had chosen poorly and that perhaps it was a poor value or would fall apart. And Akubra was mentioned time and time again as a best bang for your buck starter hat, so I figured I should check that out as well.
I guess I'm back to where I was when I started, which is to do what Glider and Jared suggested and just keep the one I like and enjoy it, and then pick up a custom hat or 3 as I need.
The answer to your question is that it is difficult to give an definitive answer. The only real way to find out is unfortunately buy it and experience the hat. I have strong bias against modern production hats (with a few exceptions).....to me they are overpriced and not good value and that stretches across all brands that I have come across. Even more true for the expensive modern Borsalinos. My one exception to this rule is Akubra. To me if you buy one on sale direct from Australia the price to quality ratio is in great balance. Good looking well made hats at a very decent price and they wear so well. I have never bought an that disappointed me and I have some 20+ years old.
I stay out of the vintage market as I agree with you it is difficult (and I lack the patience for the hunt) to discern quality and value over the internet. My vintage is restricted to buying from sources that I know and trust (mostly here in the Lounge). I have made too many 'mistakes' and wasted money on vintage hats that arrived and turned out to be crap.
Wear the hat you bought if you like the look. Put it through its paces and discover what you like about it, what works and what doesn't. Consider it part of your learning process in the world of hats.....and enjoy the process. Even if you make a mistake in your purchase it is not a 'mistake' if you learn something in the process.