I agree that Fly gloves are expensive, but I think that anything that is manufactured in a country that is not specialized in manufacturing such goods will always be priced higher than those produced in Pakistan, China, India, etc., due to higher materials costs, a higher cost of living, economies of scale for small boutique manufacturers.
There's just honestly no way that without big money backing, that these boutique companies can get away with charging $150-200 for a pair of gloves and survive, at least not right now. To put things into perspective, the top of the line training gloves that were produced in the United States (i.e. Everlast, Tuf Wear) were priced at nearly $200 in the late eighties. (Also, it should be noted that those training gloves used Horse/Hog hair which was pretty expensive to begin with, and to my knowledge FLY does not use animal hair in padding its training gloves.) With inflation, those very same gloves would cost nearly $400, and that is a glove from an established manufacturer. Those companies all ceased to produce in the US due to the fact that they could not compete with overseas manufacturers, either because they did not do enough to produce a superior product (whether this was public perception or an actual match in quality) or the public just demanding lower prices.
I've seen and felt products from Pakistan and China from the 80s. Way superior to the everyday stuff that comes in from them. My problem with Grant is that he is not the manufacturer, just another guy selling his brand. There's a ridiculous premium you pay for those gloves, and they have definitely not gotten better in terms of quality. I'm speaking about my experience with their stock gloves, not their fancy $1000 customs. I'm sure the craftsmanship and materials for those gloves is still amazing and even then, not worth it.
I've never felt a Fly glove, but they do look nice. Glad they did away with the strange backhand pattern on their training gloves, with the seemingly random stitches. I hope to give their gloves a try someday. Almost bought a pair of 12 oz velcro gloves off of eBay but it was the wrong size for me. And yes, manufacturing in Japan is probably more than in the US or UK, but Winning is an established company with a factory. As long as Winning exists, it will be the gold standard for boxing equipment, but try doing anything out of the ordinary custom wise (triple cuff, hair padding in fight gloves) and you'll see that the cost will increase very quickly.