I had a "combat" encounter in my game this weekend where the party started off with total surprise against a camp of bandits.  The party of 4 PCs and 4 NPCs were in a moderately obscured forested area, and we were 100 feet away from the bandits campfire (which had burned out) and their nearest tent.  We could not see anyone but we could hear a bandit asleep in the nearest tent.  Based on the circumstances we anticipated 8 - 12 bandits in total.  We had a level 1 ranger in his favorite terrain, a dex=16 level 1 bard, a dex=12 level 1 cleric in chain armor and a dex=9 level 1 paladin in chain armor.  The NPCs included a level 2 fighter in heavy armor and carrying a battle axe and a level 2 rogue in leather armor carrying two daggers or short swords, and two "guards".  It was twilight so we could all see our full range through the growth, but somewhat obscured.

Since we had total surprise we were in strange state of a surprise round that might continue for several more rounds.  We rolled initiative and the bandits rolled initiative.

On the party's turn I had the highest initiative as the Bard so I pulled out my crossbow and asked if I could stealth forward at my movement speed, which I decided I only needed to use 20' to bring me into normal range for my light crossbow.  I had to roll even though as far as we could tell all the Bandits were asleep.  Fortunately stealth is on my expertise list and I have a 16 dex, so I passed the stealth roll.  I took the ready action.

Then the paladin had his turn.  He wanted to move forward, with a javelin, but with heavy armor the DM said his roll would be at disadvantage, so he just stayed put.  The cleric likewise drew a light crossbow and stayed put taking the ready action.  The Ranger's turn came up and he snuck his way forward to stand beside me making a little noise and almost alerting the guard.  He drew his longbow and also took the ready action.  The Rogue went forward and disappeared into the growth.  The fighter tried to sneak forward and also made noise and drew his battle axe.  This alerted a guard out of our sight but he only listened for a moment and then went back to whatever.

By the time my turn came back around I had figured that if each of us have to roll a stealth check every time we move, we are just going to give ourselves away and not get the drop on the bandits because there were just too darn many skill check rolls that would have to go right. 

The DM did agree to let us either move half our movement and roll with advantage (if a normal check) or roll normal (if it would be with disadvantage) as we crept forward -or- we could move forward only 5' as an automatic stealth move with success.

Each "round" the DM rolled for each bandit to determine if he would wake up normally to take his turn as a sentry, or if a bandit sentry on duty to decide this six second period would be the time he decided to go back and wake his own relief.  So while we were creeping forward the sentries had a random chance of waking and walking into us.  If a sentry woke, the DM rolled a D4 to decide if he was headed N-S-E-W to go to his post.

Well, we got out of the encounter pretty well with three injured party members (2 - 6 damage) and killing eleven bandits and one got away.

So my question is, if you were the DM how would you handle this with the observation I begin with that if you have to roll too often before you can do anything of significance you're always going to fail a stealth movement.  Understand this works both ways.  How many party encampments would you roll six or more stealth checks to see if the bandits could surprise the party?  Would you require six successful stealth checks, or twelve, before a group of bandits could surprise a party using a normal watch routine?

Sounds like your GM handled it well.  You need to make a stealth check each round you're sneaking and you want to move.  You're rolling against the opponent's passive perception, which is at a -5 if they're asleep, which is a huge bonus to you.  And you had a group of six people, half of whom were wearing heavy armor and were not particularly agile, which means that, no, they should not be very good at sneaking around, even under ideal conditions.

Until the "conditions of the test" change, there should only need to be 1 stealth roll in my opinion.  The conditions change when you get into an encounter (be it a puzzle, combat, etc).  Your DM does not seem to understand how neither stealth nor surprise work.

From what you are saying, there is zero chance that the bandits could surprise you since you were all aware of them and were ready for combat.

Yes, zero chance of being surprised by the bandits in this arrangement.  But we were trying to observe them from a good position, and we were not in the position we wanted to be in for that.  But creeping to that position would be an almost certain failure if we had to roll every round.

Initially we wanted to get arranged to optimize our ranged weapons, but I also wanted to observe them to get a count of how many and see how they were armed before we initiated the encounter.  I had hopes of taking them out one at a time like the spy movies.

But like I said, this works both ways.  This weekend I was sneaking up on a bandit camp.  Next weekend bandits may be sneaking up on our camp.  So I want to be fair about this both ways.

Quote from emrfish6 >>

Until the "conditions of the test" change, there should only need to be 1 stealth roll in my opinion.  The conditions change when you get into an encounter (be it a puzzle, combat, etc).  Your DM does not seem to understand how neither stealth nor surprise work.

From what you are saying, there is zero chance that the bandits could surprise you since you were all aware of them and were ready for combat.

 
According to OP - they rolled imitative this means that yes every round you are moving you are going to be rolling.  That's the end of it.  Do i think they should have rolled for initiative that far away? Depends on the situation.  I don't think I would have made an initiative roll that early unless someone had a previously low stealth check.

Yeah, he rolled initiative too soon for you guys, it’s for combat or arguably for situations where order of operations matters... not for any tense situation where something can go wrong. There’s only one “surprise” round, and that’s the point where hostilities kick off. If you all passed stealth checks, my take would be to let you get in position. If he wanted to give each stealth check a distance value, that’s fine, but the added layer of CONSTANTLY rechecking dozens of bandits to... wake up? Move? Separately notice you? is too fiddley, and is essentially “the DM is gonna roll 10-20 dice now until he can self justify doing what he clearly has already made his mind up to do.”

Way too many checks. This might help a bit in addition to what others have said.

Group Checks

When a number of individuals are trying to accomplish something as a group, the DM might ask for a group ability check. In such a situation, the characters who are skilled at a particular task help cover those who aren't.

To make a group ability check, everyone in the group makes the ability check. If at least half the group succeeds, the whole group succeeds.

Otherwise, the group fails. Group checks don't come up very often, and they're most useful when all the characters succeed or fail as a group. For example, when adventurers are navigating a swamp, the DM might call for a group Wisdom (Survival) check to see if the characters can avoid the quicksand, sinkholes, and other natural hazards of the environment. If at least half the group succeeds, the successful characters are able to guide their companions out of danger. Otherwise, the group stumbles into one of these hazards.