These are just my opinions and should not be taken as a statement of fact:
I can't really recommended any boots. I used merrel for years, then i had 2 pairs break at the same place within a year. I moved to salomon and used the same pair for 5.5 years (yes i counted). They failed (fair play) and i replaced them with the "speedcross" trail running shoe, which lasted 6 months before delaminating. I since replaced them with the "crosshike" hiking boot, with goretex lining, but haven't used them enough to really comment. The salomon warranty was pretty quick and fairly generous - a voucher worth £80 more than i paid. I still use the running shoes but i was / am dissapointed
Massive leather boots are for professional soldiers or in the event of total social breakdown, not airsofting, imo.
I also think ankle support is massively overrated and sites insistence on using them has much more to do with a sense of aesthetic and not wanting "white trainers" then it is h&s... controversial!!!!!
When i do get wet feet most of the time its not cause i stepped in a puddle, its cause i've been walking through long wet grass. gaiters are useful for this.
For a winter airsoft boot where at most you'll be wearing them for no more than 36 hours, i would (and did) go with goretex lining. but for extended stuff, i think a non-goretex lined boot with waterproof socks are best
Ultimately i see the point of all this stuff as not getting your feet wet, rather then merely not letting water in. If you get all sweaty, your feet will get wet. as a rough rule of thumb (toe?) i advise not wearing waterproof socks till your boot is already wet. wear them till they dry out enough to replace them with a normal sock.
I get very, very sweaty so bear this in mind
There's wearing the right clothes for the weather, but really its wearing the right clothes to match the weather and the activity. For a day skirmish i wear pretty much the same stuff year round, I prefer being cold and wet to being really hot as skirmishing / anything even barely resembling physical activity warms me up, it doesn't cool me down. Same with running. I adhere to the "be bold, start cold" school of thought but i appreciate that having cold hands and toes is uniquely awful.
i always, always have spare clothes, socks and shoes for the drive home. (i also never, ever, ever wear camo outside of a site. i am very body positive so have no issues getting changed in a car park)