Kegs by far. Bottling is a reason people stop homebrewing, and I would assume bottling makes you like your fermentor less .... "uggggg, I have to bottle that batch this weekend." You don't hear keg folks say that. Also, nothing like a dry tap to get you psyched to brew another batch.
I think $300 is a good initial budget for keg system. Like anything else, you can go way over budget. With 5 or 6 taps, the kegs will run over that budget but you can add them over time if you don't want to make the full initial outlay.
I have a new CO2 tank, but I get mine refilled by a local paint ball shop that will give me back my tank. Look into that before buying something new as most shops just swap empty tanks for pre-filled used tanks. If that's the case, then avoid spending the $$ on a new tank.
I don't think you can get used corney kegs free anymore, they run $50 - $100 depending in their condition. $100 for a refurbished one from a reliable vendor. You may wish to consider some of the new kegs made for the homebrew market. Some folks take issue with the weld jobs, but I have no problems with mine.
If you are thinking 5 or 6 taps, keep in mind that mini kegs like the torpedo are reasonable priced, readily available and come in a variety of sizes. I like brewing, but if I had 240 pints in a keezer, I'd miss brewing while waiting to get through enough to make another batch. I haven't tried it with my torpedo kegs but they claim you can tap and stack their mini kegs to save space. Variety is the spice of life and if you are committing to a number of taps, why not allocate space for mini kegs for smaller experimental batches or ......
I have a 1.75 cannonball ball keg tapped with a porter from a local micro brewery I filled at growler station at my local beer distributor. I am sipping it right now.
While the freezer with a controller is certainly proven to work, I saw a DIY project where a guy removed the door from a mini fridge and framed up and built an insulated a cabinet to hold a number of kegs. While this was for lagering kegs, I see no reason why the framing couldn't be modified to add taps. I think you could get your hands on a used mini fridge for less money than the freezer, especially near a college town.
If you can dedicate some space (less kegs tapped) you can use it for lagering which opens up a whole another dimension .
A conical fermentor, IMO, really has one benefit, easy yeast harvesting, but refrigeration opens up a huge possibility of benefits that equate to a lot more enjoyment from this hobby.
