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We have all been there.  You are at the put-in, excited to get on the river and you pull on your dry top or dry suit only to get that sinking feeling when your gasket rips.
I just got off a 15 day trip and was using a brand new dry top.  On day 7 the gasket (which was made 3 months earlier) blew out when I was taking it off.  Usually I bring either a spare top or a set of gaskets but since it was brand new I didn’t think that was necessary for this trip.
Luckily, I had super glue along and managed to match the tear up and get a functioning gasket and a quick repair in about 5 minutes.  That is until the next day when another rip started about an inch from the first one.  At this point I was pretty frustrated anticipating a cold, wet rest of the trip with no functioning dry top and on closer inspection the top of the gasket was showing mini tears/scallops like you get on old gaskets ready to blow up.  I cut 2 rings off the top of the gasket to get to a more solid part of the rubber and to relieve some pressure and the top lasted the rest of the trip after a couple more super glue repairs.  To add insult to injury, the DWR totally wore off—in about 10 days.
At home I got in touch with the manufacturer and they were most helpful.  They let me know that a couple things are now in play with components of dry tops.  Because latex is an organic material, every single gasket is a little different and because the process of making gaskets has an environmental impact, as the environmental regulations get stricter, the longevity of a gasket seems to decrease.  Same with DWR.  A chemical in DWR was banned in the U.S. a couple years back and DWR has not been the same since.  Gore-tex applies DWR to their fabric at their factories and the gear manufacturer does not have a means to reapply once it wears off.   They also told me to only use 303 once a month, and I had been using it once a day thinking if a little is good, a lot is better.  Apparently, it softens and degrades the rubber if used too often, and I can attest to that!  I have not found a good way to re-apply DWR with the new environmentally friendly products either— I have tried rubbing, heating, re-applying, etc. but I think long lasting DWR is a thing of the past which is unfortunate since a lot of what allows the Goretex to breath depends on water beading on the outside of your dry gear instead of saturating the fabric which closes down the breathability.
Lesson learned from this experience:  They don’t make them like they used to and while that doesn’t make me happy, the environmental reasons for the quality drop make me accept this new norm and understand about why my things are not lasting as long as before.  I’ll choose the environment over my convenience any time.  It was also a good reminder to take some super glue along in your PFD—an added bonus is that it also works to seal cuts and cracks in feet and hands so definitely put some in your kit.
Day 4 of the trip, which was a particularly windy day, I got out of my boat to find the seat bolt and assorted other pieces rattling around on the bottom.  Lucky for me, I had 2 awesome people from JK there to put it back together almost as good as new albeit a bit loose.
Lesson learned from this experience:  Know your equipment.  Check your equipment if it’s been a while (2 years in my case) or you are going on a remote trip—screws loosen over time and bumpy drives.  Have spare parts for critical pieces of your gear.  Know how your boat is put together and what it takes to get it back together if something breaks.  Don’t expect to have people that can do these things for you on a trip; figure things out before you get in this situation and be able to get by on your own with parts that you had the forethought to bring.
What repair kit would be complete without Duct Tape?  Wrap a bit around your paddle shaft or buy a mini roll and keep it handy.  For emergency dry top/suit repair I like Gear Aid—a transparent flexible nylon patch that I have used long term on my gear.  It could also work as a temporary boat patch for a small crack if you put duct tape over it on the inside.  It does not turn sticky like some tapes so it won’t ruin your gear.  
PFDs:  When was the last time you thought about your PFD actually floating you in a rapid during a swim?  Sure, we all assume that we aren’t going to be the one that swims, but swims happen.  Manufacturers give rough estimates of how long a PFD will last but there are so many variables associated with these estimates that the only real way to tell if your jacket will float you is to swim in the thing.  If you bob along merrily with your head well out of water and are easily able to get a breath, you probably don’t need a new one.  If your mouth is at river level and it feels like you are struggling to stay on the surface, get a new jacket.  Test them on a regular basis if you don’t swim a lot—it’s fun, and it just might save your life when your really need it.  Do your friends a favor if you see that their equipment is suspect and suggest they buy a new one.  For these reasons, don’t buy a used PFD unless it has a tag on it and is new.  You have no idea looking at a PFD how old it is, where it has been, or whether or not it is serviceable.  That money you saved buying used won’t matter if you aren’t able to float when you need to.  A good thing to do when you get your new PFD is to put the purchase date on it to remind you after a year or so to test it out.  If you boat a lot, a new PFD every couple years is not out of line.
These examples are a good reminder for someone like me who tends to take things like my gear for granted to pay more attention to detail.  It is also a lesson in patience and reserving judgement and blame until all things are considered, which also happens to be a good lesson for life in general.
Happy paddling,