I tend to agree with PhatDaddy. I'd be more worried about the braking than the towing. and if your trailer has working brakes than that's not a concern. Figure 2000 lbs dry for the boat, 1000 lbs for the trailer. that's 3000 from your rated cap of 5000. Since you have the aux tranny cooling package you're fine. Don't forget that a rated cap ALWAYS has a safety factor built in... so a 5000 lb cap is probably closer to 5500-6000 lbs.. and in all cases dry weight you're still only around 3000 before gas, ice, food and tackle..... and none of those are a worry for the initial tow since you're not going to be going fishing but rather taking it home. So basically, no sweat.

Thanks
 

Thanks for the thoughtful words on this topic. I towed her back 130 miles without issue. It's a nice trailer ('99 venture tandem). I definitely felt her back there, but never felt like it was too much. I'll post pics on a different thread!!

So psyched!

^ This..