It depends. Do you want to save time or make better beer?
In terms of fermenting equipment, I think the best thing to do is get a fermentation chamber purchased/built rather than having a conical. The over all quality of your beer will drastically increase if you ferment at proper temperatures. Plus, conicals are super expensive, and if you ask me a carboy works just as well, especially if you're brewing quantity is only 5 gallons.
That being said, kegging is much easier, and quite nice. I went that way first because I thought having my beer on tap at home was one of the niftiest ideas I'd ever had, so I went with it. However, I'm still fermenting in an ice bath to maintain temperatures during fermentation. I know when I get around to controlling those temps better I'll make a higher quality beer.
In summary, I say skip the conical altogether and if you choose either kegging equipment or fermentation equipment, I don't think you can really go wrong, just depends what you're looking for. If I had to do it over again, I would have sucked it up and kept bottling in order to rig up a chest freezer as a fermentation chamber. Even if you get the kegging equipment, I say look into a cheap and easy solution to controlling fermentation temps. There are a few threads already posted about cheap ways to control temps and they shouldn't be hard to find.