I appreciate the towing advice!
Not going to lie, if there's ANYTHING I'm semi-nervous about, it's 100% towing. I will be fine on the water. Towing is terrifying. Just the thought of it.
I was the same way. Buying advice is spot on for this thread but not a lot of towing advice. Once you own the boat, take it out to a boat ramp on a weekday around 10-11am (when it should be pretty dead). Practice backing up from multiple different angles. Learn how to park with the trailer straight behind you. The most important advice is to be patient. Never rush, try not to get flustered, and try to ignore everyone else. I quickly learned I back up much better when everyone else shuts up instead of telling me what to do. Patience is the best virtue when boating/trailering. I do not have that trait but I learned it solely for my boating days. My sales guy told me to always have a case of beer on hand in case I am taking too long - toss a beer to whoever is waiting behind you. Practice makes perfect but you won't become a pro after a few hours of practice. I still have days where I look like I have no idea what I am doing, and other days it looks like I've been doing it for 20 years (going on my third season now). Use your head instead of the back-up camera - I think that was my biggest mistake at first. Using my mirrors and turning my head helped so much more than trying to do it by the camera.
Once you feel comfortable with backing up the trailer, practice loading and un-loading the boat. We used to walk the boat on and off with ropes. Good option for beginners and two people, so I would suggest starting there.
From there I would practice navigating around the dock. Remember patience is key, and only go as fast you are willing to hit the dock. For me that means neutral-reverse and no clicks on "no wake mode", basically the slowest in reverse you can go. When coming into the dock from about 50-100 yards, I do a lot of forward neutral - to neutral - back to forward neutral. This gets you in nice and slow, if you hit anything it is almost zero damage and allows your crew to tie up easily. A good practice in this regard would probably be to launch the boat, then drive it over to the loading/side dock, and then back to the ramp dock a few times.
Once you get real comfortable you can practice dropping a person off to go get the truck and then you drive the boat on the trailer. In this regard I will the truck driver (someone I trust to back up a trailer) on the back of the boat, I spin the ass end around to the end of the dock and he hops off. This is great because you never tie up, and shouldn't hold a ramp up for longer than 60 seconds. Which brings me to my next point: Learn ramp/dock etiquette!!
The most annoying thing is someone taking their sweet time on a ramp on a busy day (due to incompetence) Get in and get out as quick as possible (while taking your time). Don't launch your boat THEN load everything. Before you launch, pull to the side, check your plugs, remove tie downs, load all your crap, etc. Once you launch the boat, pull out of the ramp and park the truck. Ideally while you do this someone should drive the boat over to the loading dock. On the flip side when you come back, don't unload the boat at the dock. Get it on the truck, pull out of the ramp and into a parking space. Unload and get the boat back read for trailering from the parking spot. Do not sit in the ramp putting your straps back on.
As a side note, highly recommend some Cobra Fins to help with slow speed steering, makes a pretty big difference. For a few hundred bucks it is well worth it on a $40k investment.
Other than that, driving the boat on open water, and driving forward with a trailer is pretty darn straight forward. Enjoy and good luck!
Oh yeah - go get a truck ASAP! Last thing you want to do is rely on someone else. RAM keeps winning truck of the year with their new model, I love mine. Pretty sure you can get them for stupid cheap right now.