Hi Josh,
I hesitate to offer an opinion on your situation as I haven't done that and I'm 
no expert.  However, your reasoning seems sound and here are a few thoughts. 

I'm in favor of shortening the shaft log by cutting.  Not sure how much.  
The shaft log does not support the shaft, it only supports the seal to keep out 
water, so shortening will not weaken the log.  Shortening the log will reduce 
some of the offset angle if the log isn't truely in line with the shaft.   
Shortening the log will also reduce the amount of leverage the seal might 
impose on the log if things are misaligned.   

I think the seal rubber tube, needs two clamps, but I also think they need to 
be spaced apart.  I wonder if the seal manufacturer recommends mimimum 
dimensions for that?  Without that, I'd suggest leaving twice the minimum 
distance for two straps.

This diagram of a Catalina installation shows 1 1/2" minimum between stuffing 
box and coupling.  That's all you have.  

https://www.usedboatequipment.com/stuffing-box-maintenance/

Chuck Scheaffer Resolute 1989 C&C 34R Pasadena Md


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