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Phil,
You are right, those cross members look scary. It is a shame because the rest of the metal on the trailer doesn't look bad. I couldn't get to the link for Eastern marine, but I cannot believe your fix would cost as much as Finnegan estimates. I guess it comes down to how much you use the trailer and far far you transport your boat. If you are like me and leave your boat in the water for the season or trailer for short distances to your local waterway then I think your idea is spot on and you will probably be surprised on how long you can keep that trailer going after repairs. If you like to travel with the boat or tow on roads with a lot of steep grades or hills, then you will probably not be completely satisfied until you replace the trailer. No offense, but as for the tilt continental trailer Finnegan has, I am not a fan. I have had a couple of Whaler buddies who have that same model and they do not like them much. The tilt feature is mostly useless, and I do not like the way the bunks are positioned as without guide ons getting the boat on the trailer in a level centered fashion can take multiple attempts and on a busy weekend, people waiting to use the launch ramp can have little sense of humor or patience. I would agree that a upgraded new trailer for your boat that is set up or designed a little better would be more in the $2000-$2500 range.

Jim G.