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I have pretty much same boat as you except it's a 06 back in 2018 I put a Suzie 300 on it best thing I ever did. I ran a Yamaha 225 4stroke for 2000 hrs with no problems but it was a little underpowered when fully loaded. Go Suzuki if you can find one you won't regret it.

I can honestly tell you I bought a 2320 in 2006 brand new for $62,000 with no trailer

I think you're over thinking this it's a good possibility you could have been getting pushed by current and wind going in the same direction. I jig wire 75 percent of the time I fish, next time it happens just bump it in and out of gear

Good luck with this project, I did mine about 10 years ago if you need any info let me know, it's a project but it can be done yourself. I put (DS) Dual Switching units in for the shifting that was when I had a mechanical shifting Yamaha motor. I have since upgraded to a Suzuki fly by wire in 2018

5800 is idea

Put my 2320 on loadmaster this past summer well built trailer but they cheaped out on the winch and winch mounting plate, had to use winch and winch plate from original trailer. Sold the new replacement parts they sent me as they were still cheesier then my original stuff.

Capecodparker pm me if you want so I could give you my # if you have any questions. I had mine done cape cod way.

I can say my suzuki 300 repower cost $26,000 that's with 2 sets of fly by wire controls and the extra wire harness for the second station

I have an 2006 (2320) I bought it new with a Yamaha 225 when full of 4 to 6 people engine would work pretty hard. 3 year's ago put a suzuki 300 on it and wow what a difference. I would try and find one with a 250 at least