As for pulling your 280SS Formula. I would not expect any problem pulling it, unless you are heading for the mountains.
When they rate a vehicle for towing weight, it must be for the entire US. That means the flat lands of Florida, to the mountains of Colorado.
With a little common sense you will likely be OK for short distances.
As for the over-width. Yes, by strict DOT rules you need a wide load permit. However your boat is only 9' 2" wide, and that is up on the rub rail. Your rear transom is more like 8'. The DOT will not notice this, unless the inspector is a anal and carries 2 plumb bobs to hang down from each rub rail to get an accurate measurement.
As for a 34PC and bridge clearance. If it a older 34PC with the rear facing arch, fold down the light and you should be good to go if the trailer is a low (watch the trailer brand as some tend to build them taller). If it has radar it will need to be removed or folded back.
If it is a new 34PC with the forward facing arch it will need to be removed, or fitted with a system to fold it down such as the unit that Tim Tevlin is marketing.
I have a Formula 37PC that I have towed for nearly 2,500 miles now with great results. Prior to that I pulled a 31PC for 10 years.
BRAKES are important. Mine are electric over hydraulic disc.
Hitches are important, as is how the boat/truck sit in combination.
If you have a torsion axle trailer, it must sit level when hooked to the tow vehicle.
Email me and we can discuss more if desired.
jshelton@tds.net