Its coming up end March.. its when I check the trailer bearings, wiring , studs  etc.
 And also my life jackets.

I have 3 inflatables, with crutch staps.. If you dont have them this is the best time to put them on... A big must
 $10 to $15 , smart marine marine deals, DKM all usualy stock them.
 You will find printed on the bladder a date chart that you should fill out when checked with a felt pen...date not filled? food for thought?
This is what I do.

1/Lay them out flat and open up the Velcro...
2/Remove the canister and weight it.. if light as to the weight on the side, replace it with new canister or if anything looks suspect or feel slightest suspect.
3/ Inspect belts , catches, the bladder, stitching for anything suspect.
3/ Use the blow up tube and blow the bladder up real tight.. I let sit for 10 mins or so then manage to put in a few more blows. I then put the bladder into the spa pool turning over looking for any possible pin holes, leaks. All good  leave fully inflated for around 20/ 24 hrs (just more convenient for me than the suggested 16 hrs )
4/ Next day, if still pumped up.. see if can get any more air in by blowing.. might get tiny tiny bit.. thats normal... so all good.
5/ Deflate by pushing the end of the blow tube, fold bladder in 1/2 forcing as much air out as possible. I then fold over again getting most of the last  out. I now get a small nut that just fits inside the top of the breather.. I can press on this with my tongue and suck out the rest of the air..
If dont do it , putting everything back inside can be a mission.

Now write the checked date on the chart on the bladder...

At this point, If you are fitting a crotch strap, side the belt end out of the bladder bottom 'loop' to side the long end of the loop on the crotch strap thru the belt and replace. (I also have my Water proof VHF , EPIRP and a knife on my jacket belt.)

6/ Lay out the outside cover and lay the bladder out. Starting at the pull tag side, put the tag by the belt webbing, fold the bladder in 2 upto just before where the life jacket curves around the top.
Start at the bottom pushing the bladder hanging out in as you put the velcro side together.
Dont worry if not neat.. there is a easy way later to do that.
7/ Now start at the bottom on the blow tube side work up to where the top curves.
8/ Fold the top of the bladder , line up the strap that goes around the bladder which has velcro on, and stick to the back cove velcro. This keeps all the top stuff square.
9/ Now working either from the top or top of the curve, finish off packing the bladder away.

Your  velcroed sides will be all wonky and will be easy to slip open when dont want to.
10/ Start at the bottom, open the velcro about 2".. then at the same time side your finger up, opening the velcro, and close behind about 2 inches, keeping the edges tight right upto the top, and repeat the other side.

With the pull tag, they only fall out if the side, get accidentally  actuated, when velcros tend to open up because have not been put back neat.
Also when the bottle is stored/packed at the right height, the tab cord, reaches neatly inside to just down by the belt strap. When positioned right, all it takes is a flick of the velcro by the belt and at the same time grab pull the tag.. no digging trying to find the bloody thing..

Anyway thats how I have found the easiest way to check and put the inflatables back together nice and neat.

I rem the 1st time I did one, mission to re pack. When in use, tags fell out, velcro kept pulling open....And see this so often on boats/ crew ..and wonder just when the last time some of those jackets where actually checked...