I've been unhappy with the stock 250 outhaul since buying the boat and especially after loose footing the main but there were always other things with greater priority. The stock outhaul uses 2:1 and is next to impossible to adjust under any significant load.
The goal is simple... provide enough purchase to enable trimming the outhaul under loading up to reefing winds without suffering so much drag in the block and tackle to make the sail unable to draft the outhaul in lighter air.
The first task was to identify what space and current hardware is in use and what parts of it might work with a new design. After removing the outhaul mechanics, some observations can be made. First, a sketch of the stock setup.

Quickly noted was that the block within the mast is small and of low quality and I'm not sure to work with it or discard. Sometimes much of the purchase gained by a block is lost if the block is small and of poor quality.
Chatter on the Catalina 25/250 association seemed to suggest that a 4:1 purchase seemed reasonable but most of that was focused on the C25. The 250 has an internal outhaul and yields plenty of space to configure a cascading system up to 8:1 purchase. I decided to go with the 4:1 opinion but my hunch is that an 8:1 will be needed with the larger main of the 250. So, one additional cascaded block has been added for testing.
There is ample room in the boom to cascade another block making the purchase 8:1 but I'm doubtful that the sail could draw the outhaul in light air with that much purchase, and in fact, I'm doubtful light air will draw the 4:1 as it only reasonably well draws the 2:1 out. What might be needed with an 8:1 purchase is dual control lines with an 8:1 and 2:1 control line. I will give the 4:1 a try and if it fails to provide either enough purchase to adjust the outhaul under load or if the sail doesn't draw the 4:1 in light air, then a dual line system will be opted for. It will look like this.