Jesse,
I went through the same thing this past season. I had a 6ft rotary mower and a craftsman ridealong mower for all my mowing needs. Both are fine for what they do, but neither is great for what I wanted to do. My first thought was to buy a nice zero turn mower. From what I've been told by those who have them, it's like night and day how fast and smooth they are. That's just what I want!!!! The price tag is the big hurdle for me when what I have works right now and if I bought a zero turn, I'd want to go all out and get a good one that will last for a decade at least. That means $8,000 to $10,000 for new or a little less for used. I've seen a few amazing deals on Craigslist and in the American Classifieds, but still more then I want to spend for something that I really don't need.
Then in the spring time, I got lucky and was offered a 7ft Land Pride finish mower for $600 from a client who said he didn't use it anymore and wondered if I was interested. I hadn't really thought about a finish mower for my tractor since I really wanted a zero turn mower. The price was too good to pass up. I had to fix the flat tires and replace the blades, but otherwise, it was ready to go.
7ft is on the verge of being too big for my 35hp tractor when picking it up. Pulling it and mowing with it is easy and I think hp wise, a smaller tractor could handle it too. In fact, it pulls and cuts so easily that I'm mowing the same amount of grass in half the time compared to my 6ft rotary cutter. The results are much nicer and I'm having fun mowing with it. I think it's the four wheels at each corner that make it so much nicer to mow with because I don't have to pay attention to the deck height when going up or down. It just follows along behind me and cuts beautifuly. I can also cut in wet ground that I would sink in before with the rotary cutter. Those wheels carry all the weight of the finish mower and the tractor is lighter now.
It might not be what you're looking for, but for me, it's worked out great and I no longer have that desire to buy a zero turn mower.
Eddie