Return Plug Removal Issue

So I am opening the pool and one of my return plugs got stuck and I made a bit of a mess of things...

The plug would not unscrew and I ended up cracking it and the top broke off. I removed the return fitting so I can better grab the plug to get some leverage.
That was a mistake because now the water is leaking out and for some reason, the screws for the return fitting are not screwing back in. They just keep turning and turning. Is there a trick to screwing these in? I think it's a Jacuzzi fitting.

Also any tips for getting the old plug out? I am trying to find a tool with a square bit to try to grab and turn from the inside of the plug. I've taken a photo of the plug with the end hacksawed off and looking for a tool that fits nicely inside it.

So two issues:
1. Any tips on getting that old torn plug out?
2. Any tips on why I can re-screw the old gasket & fitting back over top of the return so it will stop leaking?

Any help would be greatly appreciated!
Jason
 

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Take the screw to hardware store and get next fatter size in same type in stainless steel. If they aren't grabbing if I understand correctly they strip easy. Not sure what ur trying to explain with the plug. Is that one you got out and theres one stuck in the pool right now?
 
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Take the screw to hardware store and get next fatter size in same type in stainless steel. If they aren't grabbing if I understand correctly they strip easy. Not sure what ur trying to explain with the plug. Is that one you got out and theres one stuck in the pool right now?

Thanks @Texas Splash and @jimmythegreek! Yes I'm still at it. Let me clarify a bit. The reason I included the photo of the sawed plug was to see if anyone has any ideas for a square tool to fit into the middle of the plug to turn the plug from the inside since the front broke off. The photo wasn't the plug I got out, it's another one I used as an example to show the size of the square. The plug is still stuck and just getting worse, I've tried some different tools and the square on the inside is starting to look more like circle as I try different tools that are just breaking it more. I need a tool that can fit into the hole and expand outward to grip so I can twist this thing off. Any ideas? Should I attempt break it/cut it off?

Regarding the return fitting cover not screwing back in, this is a strange problem. I mainly want to get this cover back on so the pool stops leaking while I figure this out. The screws don't seem to be stripped, they won't go all the way into the holes. The tips of the screws go into the holes and I turn and push but they aren't gripping. It seems using a size larger screw would just be even harder. I have tried on all 4 holes, it's just not grabbing. Is there a trick here that I'm missing?
 
Thanks guys, to clarify, the screws aren't stuck in the 4 holes around the fitting. It's the plug that's stuck which is a separate issue from the screw issue. The screw issue is that I'm not able to get the screws back in to get the intake fitting cover back on to stop the water from leaking around the fitting.

The issue with the screws is that they are not grabbing, I think I'm having trouble because I'm in the deep end and need to hold on to the edge with one hand. So I am only able to screw with one hand making it really tough to put some power behind it.
 
Reach over the edge amd lay flat on deck on ur stomach that's how I do them. Try putting a svrew in without the cover on I'd bet your not lined up with the hole.

As for a tool for the square you need a plumbers spud wrench. It's for radiators and has 2 ends with various steps and one side would fit that its square. Dont keep tryimg with the wrong took you will make it worst. Worst case you have to hacksaw 2 sections out being super careful amd collapse that piece with a flathead amd remove. Gotta stay short of the threads when doing this its tricky we call it surgery
 
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Thanks @jimmythegreek and @wireform. Jimmy, you were right, I didn't realize there is a gasket under the liner as well as on top. So all the holes weren't lined up as you said. The fitting cover hole, the outer gasket hole, the liner hole, the inside gasket hole all shifted away from the screw hole. So I managed to get 3 screws lined up and screwed in, but the 4th is giving me problems. The threaded hole seems around a half inch from where the hole on the cover and gaskets line up. If I put a thin screwdriver through the holes, I can get it into the threaded hole at a pretty heavy angle, but can't get the screw in at such a heavy angle. Very strange as it must have lined up before...

Regarding the stuck plug, I will look into trying a spud wrench and if that doesn't work, I'll resort to a careful hacksaw cut. @wireform I actually already tried cutting a square piece of wood and tried to turn the plug from the inside but the corners came off the wood pretty quickly and it rounded out. Thanks again for all the great help here!
 

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