I have kayak fished all my life and own several kayaks. I recently traded a camper trailer for a 1996 186 Champion bass boat. Boat, trailer, motor and upholstery are in excellent condition especially for the age of the boat so I want to make sure and take the best care of it I possibly can so my question is...

What are some of the things you do everytime it comes off the water, how often do you wax it, how often do you grease the trailer and what else you might do that gets over looked when maintaining a boat?

Congrats!
I like to send my boat to "D" in Sanger, he does excellent work on buffing and waxing. You can find him in the fishing-classified/Swap section here. Hes got it titled "Buffing your rig.." all caps.
After he does my boat, my routine maint. is just to wax it every 2-3 months, and then after I get off the water I usually will spray it down with the garden hose and dry and then wipe down with BassBoatSaver which is a boat cleaning spray that can be used on every single part of your boat. Carpet and upholstery too.
That's all I do cleaning wise.

If you don't have bearing buddys, I highly recommend them. I always check them before every long trip and then monthly. All depends on how much you travel. Just pump them full of grease and you'll be good.

I change my water pump every & housing every season, as well as thermostats and lower unit fluid.
I always put my boat in gear while towing just so the prop doesn't spin, not sure if it helps but its peace of mind for me.
After you pull your boat out of the water, pull out of the way of traffic, away from the ramp, and lower your motor to drain all water.
Turn headlights off at ramp when its dark.
If you are not fishing during the winter, use proper steps to winterize. If you are fishing during the winter and are not storing your boat in a climate controlled garage or shop, be sure to drain ALL water from the motor, and boat hull and check lower unit fluid if its going to freeze while not in use, if the oil is milky color, you've got water in your lower unit.

I'm probably forgetting something. Just be cautious and courteous on the water and it should be smooth sailing!

Wax will be determined by the type of wax that you use. Before you wax, you need to strip the old wax off. You can use dawn detergent for that. A good wax system will only need waxing about once a year with just routine washing in between. Just don't wash with any soap that strips wax. You can just get a spray bottle to spray on and wipe off to maintain the shine between waxings. If it has any oxidation on the paint then I'd definitely consider paying to have it buffed out the first time. A professional can get it looking new again.

Congrats

If you can, park in a garage. At least, use a quality cover.
Wax 2-3 times a year if garaged, more often if parked outside.
Use spray wax when you wipe down after loading on the trailer.
Get it serviced every year.
New water pump impeller every other year.
New trolling motor batteries every other year.
DO NOT pump grease in bearing buddies. Just have the wheel bearing serviced and check them by jacking up the wheel and spinning the wheel, if the bearing is noisy, repack or replace.
Keep it washed, including the carpet (use shop vac to dry the carpet after cleaning).
Use manufacturer recommended 2-cycle oil.
Use fuel stabilizer and de-carb additive (Yamaha ring-free, Mercury #2 fuel additive, etc.)
Replace old trailer tires as needed (even if they have good tread).
Go fishing as often as possible!!!!

Why not pump grease into the zerk fitting? Its what it is for...
I would re-pack by hand the first time and then use the bearing buddy system, just don't pump too much.
Replace trolling motor batteries every other year?!?
I must have been doing it wrong all this time then. Maintain your batteries and DO NOT replace every other year. Most trolling motor batteries can last 5-6+ years and even more. Just keep them charged.
Not sure where you've been getting your facts my friend.
Use fuel stabilizer and de-carb additive (Yamaha ring-free, Mercury #2 fuel additive, etc.)
Replace old trailer tires as needed (even if they have good tread).
Go fishing as often as possible!!!!

"Why not pump grease into the zerk fitting? Its what it is for... "
Because you can blow out the back seal.... this is a well known/documented issue.

"Replace trolling motor batteries every other year?!?
I must have been doing it wrong all this time then. Maintain your batteries and DO NOT replace every other year. Most trolling motor batteries can last 5-6+ years and even more. Just keep them charged."
Batteries die due to the number of times they are discharged and then charged (cycled). If you fish a lot and use your trolling motor a lot, they will not last 5 years. If you use your trolling motor infrequently, then they may last longer.

"Not sure where you've been getting your facts my friend."
I am pretty sure I am not your "friend".

You get beat up a lot in high school?
Calm down

Just trying make sure the correct information is dispensed. You should put the multi-meter on some of those six year old batteries and tell us what it reads.

Mine are 2 year old lithium pros... Need I say more? Do you think they need to be replaced?
But nevertheless I have owned, as well as many others have owned led and gel batteries that have lasted 5+ years, and I have had some that never went out on me but just replacing for peace of mind. In fact, their is a battery thread floating around... go take a look at it and tell me how many folks replace their batts. every other season. Hell, some are still on 4 year old batteries that are still kicking hard all day.
Also in regards to the Bearing buddies, the bra cap is there for the overfilling reason. Bearing Buddy's have an automatic pressure relief feature that prevents over-filling and over pressurization. Without this feature, the inner seal will be damaged...
You may have been using off brands.

To each his own...

Over here in Tennessee we have the best in the business. Myself and the rest of the staff at Lithium Pros take pride in our product. I believe 11 of the boats in the classic were running our stuff. We offer only the best trolling and cranking batteries. Our batteries are 100% safe as well as we use a non volatile chemistry in our batteries. The chemistry is Lithium Ion. At less than a 4th of the weight of conventional lead acid battery, those who make the switch have experienced the following: faster hole shots. 2-3 mph gain on top end. Saved space. bass boats setting 2-3 inches higher in the water. We would love to answer any question anybody may have about our product. you can reach us here in Knoxville TN 8:30am-5:30pm Monday through Friday Will@lithiumpros.com (865)688-2083.

Best regards to all,

Capt. Jerry You are correct on the bearing buddy issue. But you know that, I think Ricky hates being told he is wrong.

You may also want to keep your steering system, tilt and trim greased. Also Capt Jerry and Ricky, your nuts. You both forgot to keep your nuts tight. Wheel nuts, mounting nuts, all nuts. I also use Stabill 360 marine in every tank. Probably not the best out there but have used it in the same motor since 1991 so I cant complain.