Ofcourse asks “In the eyes of the Torah, is marrying a Jew, even a drastically less religious Jew, or a totally secular Jew, better than staying single, or vice versa? If anyone is aware of any Gedolim’s thoughts on this, please share.”
Given the topic of this thread I presume the question is whether a frum girl should marry a less religious man. I haven’t heard any Gedolim opine on this. However, I once heard that R. Ruderman told a group of bais yaakov girls (including my sister) that the reason Yaakov was punished for hiding Dina was she would have been able to be mashpia on Eisav LiTov.
So, if the frum girl would be able to keep Taharas HaMishpacha and the less frum man would agree that their children should be raised frum it seems to me like it would be ok for the frum girl to marry him. Now, of course, the devil is in the details, and it would have to be an unusual situation to work, however, in theory it might be able to work. Just my $0.02!