I wouldn't take it around Cape Horn. I don't know what my limit is yet, except that I haven't found it. In 20-25 knot winds and 4-6 foot wind waves it's a lot of fun to sail close hauled and close reach.
My boat isn't provisioned to fly reduced enough sail to point well in winds 30 knots or higher. My only option is to reef the main and run on main only. The boat sails pretty well on main only, but won't point higher than 40 degrees apparent. With a second reef and a heavy weather jib I'd feel comfortable taking it around the west coast of Vancouver Island where I can time weather somewhat, but need to prepared for bigger conditions. The same would be true for a run to the Bahamas.
It doesn't have the tankage (25 gallons water is the main limitation) for me to consider doing something like sailing to Hawaii in it. It is certainly a more robust boat than many of that have done that voyage though.
In my experience the Yankee 30 is more fun to sail is big conditions than the Pearson 28-2. It's heavy displacement (2000lbs + heavier) and less flat bottom and skeg makes it get blown around less when running downwind. When the conditions get big enough the flatter bottom after of the keel will get the Pearson surfing (exciting and fast, but requires a lot of attention) where I think it would take truly massive conditions to get the Yankee surfing. I've had the Pearson surfing to 9 knots in 3-4' waves and 20 knots of wind.
The Pearson has a larger interior than the Yankee, but both are more than enough for one or two people. On the Pearson we use the V-berth for sail storage and sleep in the "aft cabin" (really a very large quarterberth). On the Yankee you'd use cockpit lockers for sail storage and sleep in the V-berth or maybe the lowered dinette (but converting that every day would get old).
Both of them have better than average engine access, but the Yankee is a little better. It is in the center of the boat and the cabinets on pretty much all sides come off, giving you nearly 360 degree access. On the Pearson the cabinets on front, top, and behind come off, but you have more limited access to the sides.
The Yankee came with an awful set of original engines (Atomic 4 or underpowered and rare diesels), but many of them have been repowered. I have two friends with Yankee 30s, one has no engine at all, the other has a Beta 2 cylinder. Another one that was for sale here had an Atomic 4. Pearson came stock with 2GM20F.
The Yankee's achillies heel is that the decks are built with core all the way to the hull deck joint. You need to check carefully for core issues. The right fix is annoying but already done on many of them, which is to dig out the core along the edge and replace it with glass. I don't know if the similar Tartan 30 (same designer, almost same design, different builder) has the same issue or other details of how it is built (like what the chainplates are attached to). I've been impressed with the construction details and design of my Pearson. The bedding compound used has been durable, they beveled all deck holes which makes the bedding last a lot longer, the hull/deck joint is really easy to service, chainplates are inboard but go right into the hull, rigging seems oversized.
They are very different boats, but both are good boats. I'd recommend sailing or checking out both of them if you have the chance.