Do you ever require your players to make multiple skill-checks for a specific task?

I remember I was playing a Medic character and had to make numerous checks to try and stop bleeding, identify injuries, remove shrapnel and finish the operation.

Do you find that this adds anything to the experience or just slows down the game?

Normally no, but will if it can add to the story. It's also (sneakily) a way to make sure that it's not always the best person for the job that gets to do all the rolling. I had a case where the medic wanted to heal an enslaved (and maddened) Wookie, but I required another player to make a Xenology roll to even get close to it and start a conversation, and another player to make a Charm check to allow the medic to proceed.

But the Medicine check was still just one roll.

Story-wise it could be interesting if the patient had some strange condition and there were multiple medics in the party, but otherwise it just bogs the story down.

So far I've only run one of the pre-built adventures -- we did the Age of Rebellion game, and there is a speeder/AT-ST chase near the end. Generally speaking, I only ever had them do one or two checks depending on what they were doing. The guy playing the Spy was the only one on a speeder -- the other three PCs were in the AT-ST -- and he was sort of facing off against the Scout Troopers by himself. In a fit of insanity, he came up alongside one of the Troopers and decided to pull a Luke Skywalker, leaping from his bike to the back of the Trooper's bike. It turned into a game of who gets to pilot while trying to push off the other, who is also trying to push them off -- I think I ended up having them roll against each other's Brawn and if he was at the controls I had him do a piloting check, too, with difficulty because he was trying to fight off an enemy on his back.

The final piloting check led to a failure and the speeder bike taking a final strain, so it shut down -- but it was still barreling forward through the jungle since it still had lots of momentum built up. The front of the bike started to tip down and he had to figure out what to do. Instead of just jumping free, he decided he wanted to hold onto the Trooper, leap from the back of the bike, and ultimately spin the Trooper around to land on top of him to break his fall. I think I had him do... a Brawn check to be sure he held on, Athletics for the jump, and Coordination to be sure the Trooper took all damage instead of him.

It was fantastic.

Far Horizons actually calls out a surgical procedure requiring multiple rolls if so desired

This game gives more ways to skin a cat in this regards.

1. If the story is best with many dice rolls go ahead, make them.

2. If the story isn't best with multiple rolls, make just one and give a setback or two for what the other situation may be.

3. Make one dice roll, but use the roll to determine the severity of the outcome.

My PC's are about to start exploring the Na Salanor and there are lots of athletics tests to avoid falling through the floor, slipping on water and so on. I think one roll per room or area may be sufficient, just narrate based on the advantages and disadvantages rolled. A single disadvantage may be a slip and some small strain, two would be a fall through the floor and some small amount of wounds, three would be the whole floor caving in and all the party falling.

Like Amanal said, it can just depend on what makes a great experience in the game.

If it feels monotonous, like you're just rolling a series of checks without any special narration and it's boring, then you were probably better off with just one check.

But if you can suspensefully narrate what's happening between each check and how it affects the next possible action, they can be fun and exciting.

One thing I like to do is take a significant event and break it up into 2 or 3 important checks, which each go toward improving a final definitive check if they're successful, or making it worse if they're not.

I had the players' ship wrenched out of hyperspace in a planet's orbit and they found themselves entering the atmosphere without any engine power, getting faster all the time.

The crash involved 4 checks:

1. A Fear check

Each player had to make a Discipline check to avoid being overwhelmed by the terror of the situation. Failed checks meant a couple points of strain and a setback die til the end of the crash encounter.

2. Get the engine going again

The ship's mechanic had a chance to start the ship's engines. If he failed, it means the check at the end of the encounter is harder.

3. Stabilize the ship

The ship's pilot had a chance to make a Piloting check to regain control of the ship.

4. Touchdown on the planet

The last, definitive check is a Piloting check to handle the crash landing on the planet. If the other checks all passed, this check is a lot easier. If they failed, it's harder.

This could have all been handled as one Piloting check, but I drew out the tension and narrated each check to make it more suspenseful and fun.

You could do that with anything--slicing through a computer, defusing a bomb, building an explosive device, even negotiating with a crimelord.

Here are my notes for the crash landing encounter:

https://explorers-on-the-edge.obsidianportal.com/wikis/crash-landing-on-luma

Honestly, this is a question about storytelling. To decide on if an event is something worth stretching out into multiple rolls, or something worth lumping together all into one roll, ask yourself some questions:
How big a part of the story is it?
Is it an important part of the plot or theme of your game?
Does it warrant spending that amount of table time on it, and generating/spending that much advantage, threat, triumph, and despair?
Do you have a plan for what happens if they fail an intermediate step?

If the answer to most or all of those things is yes, then I say go for it. If you think about it, combat skills are one of the few moments where time gets broken down into initiative rounds and very repetitive checks are required to break down the exact series of events for specific actions, in the CRB. That is because combat is considered a very large part of the stories being told at any RPG table.

However, there is nothing stopping you from flipping this paradigm on its head for campaigns that are more mechanical or medical or social in nature, and resolve entire combats with single skill checks, and break down other elements instead, so that your game is focusing on what your game is about.

Obviously, this is a pretty radical shift, and unless your players are ready to really get into the nitty gritty of role playing whatever the new focus is other than combat, it is probably going to be a disaster. That said, if everyone is onboard, and you are making effort to vary the checks so its not just spamming Average Medical check or something, but sees use of a broad range of skills, I'd say go for it.

YTYR

Can I add option 4?

4. Multiple Rolls for one event.

Your players engine is badly damaged and they are fleeing some Imperial fighters or worse. In order to make the jump the engineer will have to repair the jump engine while in a chase with the other ships. Now, the engineer can repair the engines and you jump, but that is very ordinary. Why not have the engineer require say 10-15 successes to repair the engine, a process that will take a few turns of the chase.

If you allow the Engineer to use the advantages and triumphs on affecting the chase he not only gets the tension from the chase but the work he is doing can relieve the ship's system strain, improve shields, give a boost to other players actions and tests.

Within a small party no one should ever be left out of space combat and this setup will help a non-pilot/non-gunner player start to discover how he can impact in a positive way on the narrative and participate in the event/encounter.