Cascade 29 upgrades to bluewater, what first?

[mitiempo]

I don't think tha Cascade 29 is that bad a choice for a budget ocean cruiser. Admittedly some were home built so that is certainly a consideration. But the boat was marketed as a budget ocean cruiser. And using the sailcalc Sail Calculator Pro v3.53 - 2000+ boats
to compare it to another fin keel/spade rudder boat of the same era, the Cal 40, the Cascade comes out rather well. Other than the obvious size difference, the Cascade shows a capsize ratio of 1.6 vs the Cal at 1.76 (under 2 is good), slightly heavier for d/l ratio at 274 vs the Cal at 248, and motion comfort at 31+ for the Cascade and a close 29+ for the Cal. I'm not saying the Cascade is as good as a Cal 40, but it isn't that bad. I notice the original poster is in Hawaii. Did you buy the boat there? Was it sailed there or was it shipped? My guess is the latter. But I think your budget is a bit tight. Rigging should be your first expense, replacing anything that is suspect (all if your budget allowed), followed by the engine - I'd keep the inboard as outboards don't work very well in a sea on a 30' boat. Any deck fittings should be rebedded if needed - that's mostly labor. If you keep things simple it's good for the budget as well. But I think it has potential for what you want to do with it. More issues with being old than with bad design I think.
Brian