You seem to have missed a critical part of sneak attack, and you seem to not understand the mechanics of grappling in much detail.
I'll deal with Sneak Attack first. I DM for a group that includes a rogue. He has been able to sneak attack about 95 % of his turns in combat so far, for one simple reason: the group has a tank that stands next to the enemies. The important part of Sneak Attack is as follows:
You don't need advantage on the attack roll if another enemy of the target is within 5 feet of it, that enemy isn't incapacitated, and you don't have disadvantage on the attack roll
If your group has a tank, they are most likely going to stand next to the enemies. Just make sure you're attacking the enemies next to your tank, and you sneak attacks are going to be available pretty much every turn.
Now, on to grappling.
Grappling can never activate sneak attack, since they are special melee attacks, not special melee weapon attacks. Grappling replaces one of your normal attacks when you initiate the grapple. Once you have grappled the enemy, you don't have to commit anything on your turn to keep the grapple going. There are two ways a grapple can end: If you intentionally let go of the target, or if they try to break free. The first option requires that you actually say that you let go of the enemy. The second option forces you to do an opposed athletics check, but on their turn, using their action. Once you have grappled your target, you can use your action on subsequent turns to attack them. If you have the grappler feat, or if an ally is within 5 feet of the enemy (likely the tank of your group, if you do a bit of team coordination), you will be able to sneak attack them.
Your build seems to be trying to solve a problem that, for the most part, doesn't exist if you play in a group. Simply coordinating with your tank so you're attacking enemies within 5 feet of them will activate your sneak attack every time, unless you have disadvantage. Rogues in 5e are balanced around being able to sneak attack pretty much every turn. If they can't, they fall behind on damage compared to even the most tank-focused of fighters.
In 5e, there is no such thing as "touch AC", so a hit is a hit is a hit.
A 'hit' is defined as (PH page 194):
If the total of the roll plus modifiers equals or exceeds the target's Armor Class (AC), the attack hits.
Causing damage doesn't always mean a hit, and not all hits cause damage. Certain spells, class features, magic items, immunities and so on can (partially) negate the damage of a successful hit. But negating the damage doesn't make a hit a miss.
Best Answer
No, a successful grapple attempt does not count as a hit.
Although a grapple attempt is called a "special melee attack," it uses a contested ability check (a contest) instead of an attack roll and, as such, does not result in either a hit or a miss (which are terms exclusively associated with attack rolls).
This ruling is confirmed by Jeremy Crawford in the Sage Advice Compendium:
If it isn't a "hit," what is it?
The correct term for a successful grapple is merely a "success," according to the following rules of ability checks from the SRD (emphasis mine).
If it's a kind of attack, isn't the roll an attack roll by definition?
For clarification on the intent behind the written rule, see this response by Jeremy Crawford to a similar question on Twitter.