How much can a 94 LC pull on a regular basis?

I have a 94 cruise that runs great, but I have a concern. I pull a ski boat with it that it does ok with (3400 lbs gross). I pull it through hills and its not great, but its not to bad. I am now beginning to start using a 2nd boat that has a gross of about 5000 lbs. It pulls it ok again, but the hills are tough. I want to see if anyone has used a cruiser to pull this amount of weight on a regular basis(I pull 2-3 times a week with a total distance of 30 miles) without problems. I feel the motor will hold up, but will the tranny. I appreciate all response.

94' was the last year for the "big" trans. 95 on got the much smaller and weaker A340. the A442 was used in micro buses in Japan. You won't have a problem with it. I tow a 4300lb truck + the weight of the trailer, about 5500lb total I would guess. Usually just locally but have been on 800 miles trips towing it.
Clifton

Thanks for the response. I have been pulling 5k for about a month now and it seems to perform well. I feel better now, knowing it should hold up. John