i am sure you are experienced enough towing and launching a boat like you already know it takes practice with anything new . i have had a few diffrent boats over the years and have only gotten better at operating and trailering each one . it takes me no longer than a minute to put the boat on the trailer and less to take off ( yes i do get bored and time myself ) . i love fountain boats with a passion because of how they ride , handle and are made not to mention going faster with stock power than everyone else . i would be a little scared to run not great gas in 525's but 525's are proably the best go fast motor out there when it comes to turn key and drive . i have a 93 and it has been used alot but looks and works wonderful , don't forget b o a t break out another thousand cause its true but if thats your passion who cares . where i live i see people with all diffrent sizes of boats up to 38 feet launch at public launches with out issue , if i were you i would talk to people who have larger boats where you want to use yours and ask them questions like where they launch and what not . i have no idea where you want to use this boat but for me a 27 foot is a relatively large run about which works great for windy days or weather that sucks i would love to have something bigger but checkbook is just not there yet ! lastly make sure you have someone who knows boats check out the boat and trailer before you buy and if repairs need to be made put everything in writing before hand . most trailers work really well for the size of boat they trailer if they are maintained like the brakes , bearings and tires if a trailer is in good working your truck will work well i think .