I removed my centerboard last year and cleaned out the housing completely to meet the TRPA inspection criteria here in Tahoe. It was not difficult if you have the right equipment and know how but the centerboard does weight a lot on the 260 (I am not sure about the 26). It would never float up into the housing when sailing as you said happens on the 26, but it may pivot back and forth slightly if not cleated. The whole operation took about 2Hrs on my own and I recall the most difficult part in fact was getting the newly tied knot to sit flush intio the CB.
There was a lot of growth inside the housing so you should consider the history of your boat and the last time the line was changed. Mine came from a lake in OK and a significant amount of dirt covered the keel. It was impossible to get to see this area when the boat was on the trailer.
I am 100% certain that my new lift line is set correctly and though it requires a significant amount of power for me to pull this up, I can do this manually and without using the winch, normally I put my foot against the bulkhead to give me better balance. If you can only lift using the winch something is definitely wrong.
There are a few factors I can think of that could inhibit the motion:
1) Worn line that has jumped off the roller
2) Incorrect OD line. I purchased the 7/16th line from this site to make sure it was correct and had no stretch.
3) Stuck or damaged roller
4) Excessive growth in the CB housing restricting it
A couple of tips if you do remove the centerboard.
1) Lift the table out the way and tie it with a ratchet strap to the ceiling
2) Before lowering anything, Insert a long 3/4 inch all thread once you remove the bolt. This will allow you to control lowering (and lifting) the CB at the pivot point. I used rgranger/ crazy daves pdf above am my guideline. I think the main difference was that I used pallet racks secured in concrete as a lifting frame and 4 X chain blocks. The boat lifted very easily from the trailer.