re: Need help, I’m retiling my bathroom

Remove everything down to the wood layer. Then examine the wood for structural integrity. If not good, evaluate for either replacing bad parts or just doing a layover with plywood. Need to make sure your subfloor is still good. Once you've done that, or determined it was good to begin with, use floor leveler to level everything out. Then lay sheets of duroc, it's like a cement board, comes in 3x5 sheets, and is designed to put tiles on. Make sure you glue that down and screw it in...that will seal everything together tight and give you a solid floor that won't creak or move much....a solid foundation to lay tile on.

The more you remove, the more you’ll have to patch. So the less you gouge, the better.

Keep chiseling. Its a bitch but it has to come out.

Then pour self leveling concrete over it. Just enough to get it level.

Then retile. If on a house that has any slab cracks I would put down an uncoupling membrane (such as Ditra). Or if you are on a wood foundation (wood floors) you will need Ditra for sure.

If you are on wood floor make sure that there is not any deflection or tile will crack. Here is a calculator to determine if you need to firm up the joists. Old school stuff had a 2-3" mud bed which did not allow any deflection but todays way is with a thin tile backer and if floor moves at all it will crack.

Deflection calculator LINK

Good luck

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Can I fill in the hole where it went down to the wood with the same leveling stuff? It seems easier to rip it all out vs skimming the tile off the top to be honest

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MAPEI Self Leveler Plus can be installed from 1/8-in up to 1-in in a single pour. Consider the total depth of the layer of self leveler, layer of thin set, and new tile thickness.

Surely retiling a bathroom can’t be this damned dangerous/complicated

You’re going to destroy the plywood with that tool. Just crack the mud floor with it and pry up the old mud floor in chunks using a crow bar.

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shite baw, you retiling or digging a tunnel?

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The tile would come up otherwise. Was stuck on there good

Had one similar, I ripped mine all the way to the joists, put new sub-floor down, then installed the KERDI tile system on top before laying the tile. Won't have to touch it again.

ETA: The sub-floor was rotted underneath, as your will likely be.

If you are going down to the plywood, I would recommend that once there that you use a leveling compound on the entire area you plan on tiling. To do that, you need to get as much of the old material up as possible. Next you will need to use the recommended floor pre adhesive that goes with your leveling compound. This is essential because is binds it to the wood. Once the floor is level and dry, You will need to install Hardy backer board over the subfloor. This is highly recommended because it repels moisture and prevents mold growth (remember this is a bathroom with lots of moisture in the air). Once the backer board is in place, you will lay the tile on it.

Edit: A few other notes because I went through this process myself last summer. First, when using the leveling compound, especially in a big area, use an adjustable leveling rake. its generally easy to work with, but if you don't use a rake you are going to end up with high and low spots, and you're going to notice them when you go to lay tile. Secondly, test fit and number your backer board pieces so you know where they go and are comfortable maneuvering them into place. Thin set dries quick, so if you're not comfortable getting them in place, its going to dry out on you. You also need someone drilling the green floor screws in as it's laid in place. This will ensure the backer board bonds to the thin set. Don't drive them in at an angle or leave them sticking up. This will throw your tiles out of level. Finally, use a level and check all over your floor to make sure its level and there are no high or low spots. If you make it to this point and all is good, square off the room for tiling