My Contessa was rigged by a previous owner, so I can tell you how it is presently setup and what I'd prefer.
My current mast runs internal halyards with exit sheaves at the very bottom of the mast. The halyards run to turning blocks on deck and back to the cockpit, passing through individual clutcesh and lead to winches (main halyard to port, Jib & spin to starboard)
The boom topping lift is internal to the mast and exits about 4' about he deck through a keyhole shaped hole (a stopper knot is used).
We have a winch on the mast, under the boom, for the outhaul and 2 reefing outhauls; All three are run through the boom, around turning blocks to the appropriate clews.
Here's where the opinions come in...
1. Running the halyards back to the cockpit is safest as I don't have to send crew or myself around the dodger to raise the main or jib. However, this setup does induce friction because of old sheeves and turning blocks but does allow them to be properly tensioned with a winch.
2. Internal halyards that exit at the base of a mast are a nuisance and I don't like them. When working the foredeck of race boats, I can tell you it is much easier to jump a halyard that exits the mast above head height so that you can use your body weight to hoist quickly with full range of motion. Halyards at the base of the mast require that you are trying to grasp the line and pull up, using your back instead of your body's gravity.
3. Having the Outhauls at the mast and the halyards in the cockpit is at odds & evens. Why would they do this??? it makes no sense for a single handed person to try to lower the halyard in the cockpit, race forward to put the tack rings on the hooks, race back to the cockpit to raise the halyard, then get back to the mast to tension the outhaul. It is far too many fore/after trips and should be re-rigged so that it can either be all done at the mast OR all done in the cocklit.
The answer, for you, is going to depend on your boat, your philosophy and your budget.
a. Are your halyards run internally or externally? Do they exit above deck or at the base of the mast?
b. Do your halyards exit both sides of the mast or only one? Do you care about winches (i.e. Do you require 0, 1 or 2 winches on the mast?)
c. Do you prefer all lines run to the cockpit or do you like to keep everything off the deck and at the mast?
d. Are you single handing or will you have crew that can go forwards while you steer?
Basically, at cheapest you CAN get away with nothing more than a few cleats on the mast. You can get more expensive with 3 halyards run to the cockpit, 3 outhauls run to the cockpit, you'd need 2 x 3sheeve turning blocks, 6 clutches and two or 3 winches...
My personal opinion is that having 4 - 6 winches in the cockpit is best. You never know if one jams up and you need to run a line to a spare winch or maybe you're flying a kite, then you can use a lazy-sheet setup. And having someone grind you up the mast on a halyard is possible with a winch, but not if you are merely jumping the halyard by hand.