Koz

Before I bought my winch and post assembly I would pull my kayak onto my trailer with a dock line. That was a chore because my fully loaded AP is hundreds of pounds and it wasn’t easy pulling it up over the bunks.
 
Now I just attach the winch line, crank the handle and quickly and easily pull it up onto my trailer. That gets me away from the ramp much quicker so I’m not blocking other boaters AND I’m not worn out wrestling my kayak.
 
Tomorrow I will post a picture of my winch assembly. I bought the winch and post combo in the link below, but I did use different u-bolts that I picked up for a few bucks at Lowe’s.
 
If you buy one, just make sure you get the correct tongue size.
 
One more thing - backing up a short trailer is not as easy as backing up a longer trailer. To combat that I bought a tongue extender. 
 
https://www.boattrailerpartsplace.com/shop-trailer-parts/winch-post-winches/winch-post-assemblies/winch-post-assembly-2x2/
 
 
 

I have a Helix 7 and I run a Nermak 12V 10aH battery. I paid $49 for it bit it's now only $39:
 
https://www.amazon.com/gp/product/B097BRKCQP/ref=ppx_yo_dt_b_search_asin_title?ie=UTF8&th=1
 
I previously had a Hook2 5 and used a 12V 7aH Dakota Lithium that I bought for $69. Dakota makes a great battery, but they are pricey. I will probably end up using that battery to power my navigation and deck lighting.

I think you can fit a milk crate back there. Sure, you could use a zippered bag or backpack, but very quickly you're going to get tired of reaching back, pulling it out from under the bungees, swapping baits, then reaching back and putting it under the bungees again.
 
If a milk crate doesn't fit try a cheap storage bin like the one in the link below. Ditch the top so you can just reach back and grab one of your plano boxes out of it.
 
https://www.walmart.com/ip/Hefty-18-Qt-Clear-Storage-Bin-with-Blue-HI-RISE-Lid/245902327
 
I'm lucky that not only does a milk crate fit easily in the back of my yak, but I can also slide 2-3 boxes under my seat.