I have two 235 engines here ant I'm still contemplating which one to rebuild. I have a 55-57 solid cam motor and a 58-62 hydraulic. I was on EGGE Machine's website and I saw they have a listing for a 261 cam. I know it will work in the 58-62 block, but will it work in the 55-57?
=> Yes it will work in either block.

Will I need some additional machining?
=> No. Just make sure you have the correct mechanical lifters and push rods for the 55-57 block.

Will I need to install some heavier valve springs on either one?
=> Most likely this does not matter but you could contact Patrick's about heavier springs (he sells them, so he will recommend them). Also, ask EGGE.

Or am I just better off sticking with the stock bumpstick and forgetting the hassle for just a few measly horsepower?
=> It's your choice and your money. Most likely you will not know how much difference it made (relative to the benefits of having your engine rebuilt). Is it worth doing so that you have a topic for conversation and speculation?