D&D 5E How would this rogue play?

That is not what Grappler does.

You are correct, Grappler is horrible, I got it confused with the Tavern Brawler feat which does allow the stated ability and lets you add +1 to strength or constitution. I corrected my original post.
 
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You are correct, Grappler is horrible, I got it confused with the Tavern Brawler feat which does allow the stated ability and lets you add +1 to strength or constitution. I corrected my original post.

Tavern Brawler doesn't do that either.

The bonus action grapple can't be done with a shove (unless they have 2 attacks)
 

Tavern Brawler doesn't do that either.

The bonus action grapple can't be done with a shove (unless they have 2 attacks)

I can see there being an argument made that a shove is an unarmed attack, BUT I would also say due to the statement by the OP "the thought was to go with heavier armor (up to half plate) armor" getting 2 levels in fighter for actions surge and medium armor (since rogues only have light) would be a path they want to take and would allow Tavern Brawler used under your stated restriction. Of course 5 levels of fighter would be better for extra attack to make it more dependable. Might as well grab the 2 handed fighting style for that off hand short sword along the way.
 
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I can see there being an argument made that a shove is an unarmed attack, BUT I would also say due to the statement by the OP "the thought was to go with heavier armor (up to half plate) armor" getting 2 levels in fighter for actions surge and medium armor (since rogues only have light) would be a path they want to take and would allow Tavern Brawler used under your stated restriction. Of course 5 levels of fighter would be better for extra attack to make it more dependable. Might as well grab the 2 handed fighting style for that off hand short sword along the way.

Sorry if I was not specific. Character is going to be mountain dwarf and will have armor that way.

The reason for grappler is simply to be able to set up sneak attacks even if I am alone. I will generally have them just for being with allies.

Lastly, enjoying every post but I want single class rogue and will only have one attack so some maneuvers suggested won't work.

And the main issue missed by most: I was thinking grappler because it gives advantage. Normal grappling does not, so I think this is key.
 

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