Welcome to Sailing and more specifically DaySailering! Your boat looks to be in great condition, just needs some cleaning and maybe a bit of paint. Two suggestions:
1) If you are going to trailer the boat any longer distances (over 1/2 hour or so), then repack your bearings sooner rather than later. That trailer looks a bit "worn" and gawd only knows when the bearings were last checked. You don't want to be stuck by the side of the road with 600lbs of boat sitting on a burnt-out hub! I wrote a quick how-to down below.
2) Your jib sheets... going thru a fixed block then the cleats to leeward can be dangerous. Why? Cuz you''ll cleat down the sheet and it will be over on the other side of the boat when you may need to uncleat them in a hurry fast. As in, when you are caught in a hard gust and about to capsize. Check the various discussions on this board about ratchet blocks, Greenlake converted a lot of folks including me to ratchet blocks for the jib. With ratchet blocks, you can hand-hold the jib sheet easily. And most ppl then cleat at the centerboard, if they cleat at all.
GL already mentioned your lack of centerboard thwarts. Certainly something to keep an eye on!
Fair winds,
Tom
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How to repack trailer bearings:
...Apologies if I'm preaching to the choir here. If you've done car or motorcycle work, this is "old hat."
-Jack up the trailer, put blocks under the frame (trailer jacks, cinder blocks, 8x8''s, whatever is sturdy). Take the wheels off. Helps if you loosen the nuts half a turn before you jack up the trailer! How are those tires looking? Inspect, replace as needed.
-Knock the Bearing Buddy covers off (those look like Bearing Buddy's in your photos). You need to do it with a good mallet, you walk them off the hubs by knocking on alternate sides, see youtube on how. Bang 'em HARD and be patient. A 3lb Deadblow mallet is the best for this. It's kind of like taking a stuck cork off a bottle.
-Unscrew the crown nut, you'll have to remove the cotter pin first. Next take the entire hub off the spindle and haul it over to your workbench. Scoop out the old grease till you get to the conical bearing, take that out, scoop out the rest of the grease.
-Clean everything, get the old grease off as best possible. Plenty of paper towels (about an entire roll), and either kerosene (less corrosive, takes longer) or spray-on brake cleaner fluid (try not to breathe it in, dont get it on your skin, but works fast). Clean the spindle too (the part that the hub sat on)
-Visually inspect for any issues - This is the most important part, you want peace of mind. Are there any gouges on the internal surfaces where the bearing sits? If yes, that's a bad sign, at least replace the conical bearing. Is there a lot of grit in the old grease? Bad news, see if you can figure out what broke in there. Is there any purplish discoloration to the metal on the bearing? That means that it overheated at some point, replace it. How does the back bearing look? It's a flat bearing, sealed in by a set of rings. I usually dont take it out, but I want to make sure it's spinning well and no discolorations or weird noises as it spins. Youtube on how to get it out, if you need to.
-If all is well, then grease the spindle, pack grease by hand onto the back of the hub, put hub back on spindle, pack in some more grease, grease the conical bearing (look on youtube how to do that properly), put the conical bearing back in, more grease, put the flat washer onto the conical bearing, with the groove facing INWARDS, bit more grease, castle nut, tighten it properly (youtube again, there's a trick to how much to tighten it), more grease. You can pack all this grease in with your fingers and hands.
-Put the Bearing Buddy back over the hub, put a small wood plank/offcut over the face of the Buddy (to spread the load) and then hammer it home. You should have packed in enough grease that a little but will get pushed out of the Buddy-to-hub seal when you hammer it home.
-Wheels back on, tighten lug nuts, trailer back down to ground, done!
Some notes: You can get everything you need either online (etrailer.com) or at local autoparts store. I like O'Reilly's. You'll probably want to get new cotter pins, $3 for a set and saves you some frustration. Wear latex gloves, and old clothes, you will get filthy! Sugar gets grease off your skin. Put old newspaper down on the ground while you are taking apart/putting together the hub, that way anything that falls wont get crud in it. Use MARINE grease, marked "for boat trailers", not regular car grease. You can figure it all out from google/youtube and common sense. In theory, instead of packing the grease in with your fingers, you should use a grease gun and push it in via the Zerk fitting (yup, that's what it's called!). IMHO, not worth the bother, but if you know someone with a grease gun..... And again, you can get anything, even a new axle, online and relatively cheap. Peace of mind while trailering is everything, so if it looks suspicious, replace it! Check the trailer wiring while you're at it
