Yeah, unfortunately he's doing everything he can to prove he's not capable of taking care of himself. Getting dentures isn't going to be as easy as he thinks, too. It will be a process that I'm willing to bet he's too stupid/lazy to follow. He will probably need to be on an antibiotics cycle leading to the extraction, so his gums are manageable. He will also likely need a bone graft procedure to even support dentures at this point. I'm sure it will be multiple visits and Clint will have to hold his hand every step of the way.
I've mentioned before that i used to be adental assistant, and you hit the nail on the head over all those points.
His mouth is so bad at this point, it wont be a simple fix. He first needs a general appointment for an examine and x-rays, he will be perscribed antibiotics at this point. No sane doctor will attempt to extract right away untill the infection is manageable. They will probably do a deep cleaning (Scaling and root planing) and maybe even a lasar treatment on the periodontal pockets to clear them of tartar, pus, and any diseased tissue.
While the antibiotics kick in, he would need to follow a strict teeth hygiene routine. Brushing 2-3 a day, periodontal or salt rinse after every meal, flossing right before bed, and preferably a water pik to reach under the gums.
His second visit would be the extractions. This could be done all in one visit, but if his teeth are so brittle that they begin crumbling and leaving roots stuck deep within the gums, he may be referred to an oral surgeon to surgically extract them. This may take several appointments as it's more difficult.
He would then have to heal from this, and continue his mouthwash and antibiotics.
Next step would be adding bone grafts deep under his gums where the gingivitis would have eaten away at his jaw bone. This can be done with a sythetic graft that stimulates bone growth, donor bone from somewhere on his body or even cadaver tissue (how gothic twu) healing from this can take anywjere from two weeks to several months.
At that point, he can finally get dentures. If he is lucky and if the grafts take well enough, possibly implants