Can you replace that flange with a newer style retrofit flange?
The new style goes inside the pipe

 

Yes, there is a flange that seals on the outside of the pipe. Those hex bolt heads are for compressing the rubber gasket around the pipe- as you tighten the bolts it draw a collar up on the outside
You should not need the brass ring if the CI ring is at the right height and the bolt slots are okay.
Did you pinpoint the leak to the gasket at the pipe or is it from the flange/subfloor (bad bowl wax)?

 

Yes, there is a flange that seals on the outside of the pipe. Those hex bolt heads are for compressing the rubber gasket around the pipe- as you tighten the bolts it draw a collar up on the outside
You should not need the brass ring if the CI ring is at the right height and the bolt slots are okay.
Did you pinpoint the leak to the gasket at the pipe or is it from the flange/subfloor (bad bowl wax)?

This is super helpful, thank you. Based on the saturation i saw below I'm 90% sure its base bowl/wax failure. I also just put some water directly in that crack between the drain pipe and the flange and didn't see any leaking below.

I also totally missed that that the red piece (i think you're calling that the Cl ring?) has bolt slots. I just tested them and they work fine. The top of that red surface is sitting about 3/8 below the surface of the tile. I am guessing this means I can just inspect the toilet bowl for cracks and then proceed as usual with a subflush flange? I bought a Danco Perfect Seal from Home Depot which allegedly works with flanges as low as 1.5inches below the finished floor. Do you have thoughts on how well Danco Perfect Seals work? I'm a very competent carpenter but have never ventured into plumbing and have never replaced a wax ring.

Attached photo showing below

 

@TheEplumber would it still be advisable to use a wax ring with a bell?

 

I'm guessing you have something very similar to this- https://www.amazon.com/Oatey-42255-Closet-Flange-4-Inch/dp/B001REGQXI

I would verify that it is well anchored to the floor- no movement. Also be sure the flange itself is not cracked. The flange holds the toilet still and in turn keeps the bowl wax from being compromised.
I don't use any bowl wax except the type with the horn/bell embedded into the wax or the old style. Not because I don't trust other styles, I just haven't tried them... Others have and give good reviews, so that choice is up to you

 

Flange is anchored solid and appears to be crack free. I'm going to proceed with the Danco Perfect Seal. Wish me luck. Just need to get all this old silicone off the tile first.

 

I've used these for several different toilet installations and they haven't failed yet. They come in 3 sizes (3", 4", and some weird version that goes outside the pipe somehow). Much easier to use than a wax ring.

Fernco 3 in. PVC Wax Free Toilet Seal FTS-3 - The Home Depot

Attach this Unbranded PVC Wax Free Seal at the bottom of toilet. Easy to install and perfect to fit with several toilets.

www.homedepot.com

 

Poking around on Terry Love forums it sounds like what I need is a "dutchman". One other has had success cutting a short piece of 4" PVC to fit inside and using PL to hold it in place.

I have a plumber I use for bigger projects and he says he sees this issue all the time and can come by Thursday to fix it. I think I'm just going to let him...

 

Try a Fernco seal. "Accommodates floors raised above the toilet flange by up to 3/4" according to their website. The idea is that the part with the "barbs" goes inside the pipe, and the upper part sticks to the bottom of the toilet. So there is no need for the rubber seal to be as large as the flange.

 

Here is a picture of the plumbers solution. I unfortunately was gone while he was here so I didn't get to ask any questions. I appreciate everyone's help.

 

What is that called? A "flange extension"?

 

Unless that is a removable seal, those 3 allen head screws won't let the bell of a normal wax seal go down. Or is the picture taken afterwards with the seal in place?

 

Unless that is a removable seal, those 3 allen head screws won't let the bell of a normal wax seal go down. Or is the picture taken afterwards with the seal in place?

@chandler48 The first photo shows the wax ring in place.

The original flange is already sealing to the drain pipe, so the only seal left is between the toilet and the top of this black flange, correct? As long as the wax ring is properly sealing around that there shouldn't be any additional leak points?

The toilet is already back in place. I haven't done extensively leak testing on it yet