It might be best to back up the question a bit. What you gotta have is an up-angle of several degrees for the sheet lead into the winch drum.
If the line "approach" is too near to flat, you will get overrides on the drum.
I had this problem often with the stock sheet winch location on the flat part of the rear side deck on the Olson. I and quite a few other owners have put risers (or a plinth, great word BTW) under each winch. This 99% ended our problem with overrides.
So first, check the path of the sheet from the last block to the bottom of the knurled drum part of your winch.
There is a "plan B" for this: put an angled riser under the winch so the the winch itself is tilted away from the sheet lead. This gives the desired angle, but may look slightly odd on some boats, and also may may wielding the winch handle a little awkward.
As long as the coring is solid under the winch and you have backing plates or over size washers the deck will be plenty strong enough.
Our project:
Since Olson 34's are rather rare, only 39 having been built, I have a current project that I thought I would write up as a sort of trial blog. Perhaps this should be somewhere in the Maint. Forum, but with only 38 other Olson 34's in the world...
ericsonyachts.org
I had a great lunch with Paul L, visiting our fair city for a few days on personal business. We got to talking about our Olsons (what a coincidence...) and then I gave him the nickel tour of our boat. Surprising what one finds out, in casual...
ericsonyachts.org
This weekend, after having the winch project take a back seat to other events... like the EY Rendezvous and our continuing road trip around the Olympic Peninsula for a week... I got some of the mounting holes drilled for the new risers. No matter...
ericsonyachts.org
We are closer to being done. One winch is in. All I need is another break in the rain showers to get the other three on. I have some pics now of the one finished secondary winch in place. Also some pics of the molds and one extra foam plug. In...
ericsonyachts.org
https://ericsonyachts.org/ie/threads/olson-34-reno-projects.9853/#post-66550 (see reply 13)