> More realistically, if the 20% improve their game in one area the 80% are just going to one up them.
How are the 80% going to one up them? One thing about dating apps for straight people is that you don't know what your competitors are doing. If the 20% up their game, most of the 80% won't know how. Also, remember that there is a 20% for women as well. I know that standards for men are crazy high on dating apps, but I also know some of the 20% women. They usually don't end up with the 80% men, and they often end up with men who are AWFUL (not just in terms of looks). 20% men can date 20% women.
> Someone lacking in confidence and small talk type skills isn't likely to naturally get better
I agree that small talk takes some work (just like becoming funny), but confidence is truly something you fake until you make. If you act confident, people will think you're confident. Then you pick up on people thinking you're confident, and that makes you feel even more confident. If you don't act confident, people won't think you're confident, and that will be one more thing holding you back from being confident.
I'm am not naturally confident. I've had my fair share of self esteem issues and have doubted myself on many other fronts. Fake it till you make it is terrible advice for a lot of things, and you also shouldn't always fake confidence (sometimes it's good to let it all out), but if you start faking it (especially with people you don't already know), you will make it.