I actually DO quite enjoy ripping timber, but then I have a very old correctly designed diston ripsaw, freshly sharp, it rips very efficiently and is a pleasure to use.
I also have an excellent well-sharpened ripsaw, but I still hate ripping, and find it anything but pleasurable. I enjoy it about as much as I enjoy cross-country running, ie only slightly less than being hit repeatedly with a stick. At least in hardwood at anything over 3/4". My bandsaw is the only machine that, if I couldn't have it, would make me want to consider giving up woodworking altogether....
RE old and new new tools, mine are a total mix. I have quite a few old woodies, but also some stuff by Veritas and Clifton. Some old tools are better, some new tools are better, and sometimes when I've been buying I haven't had the budget to choose anyway. I don't really get the tool **** thing — I don't get much of thrill from how the thing looks (though I draw the line at plastic handles on chisels and planes) but I care a lot about how it is going to help me to make the thing I am making look good....