Agree with a lot of posters here:
Fair statement about people being meikel because they simply disregard halakha and also about being meikel with chochma often helps.
Totally disagree that someone who learns whole life gets in a better olam habo. For example, Issachar/Zevulun partnership means that both get the same one, as far as I know. So, anyone who works and support the other one (either directly or pays full, or close to, tuition at Jewish schools thus supporting both those who teach and who do not pay much) should get a share of each person they support. I don’t know hw olam habo maths work, but this can add up to a bigger share.
But biggest issue is – meikel/machmir in what? If the Yoshon Reuven above is also a baal chesed, tzedokah, davens w/ kavana, etc, this is one thing, but if he is not a good husbanf, father, neighbor, co-worker – then not.