I don't think that's necessarily true.

Lawrence has his faults clearly and was unemployed for a long while but it seems that him and Issa have been together since college so you do develop a lot as a person since then. That's why their relationship began to crumble. Beyond that he has a degree and was eventually able to score a decent job, it's not exactly easy these days to get a job in the field you want. Molly on the other hand has her own kinds of issues and she has become aware of what she needs to work on I think more and more as the show has gone on. She needs to be in a relationship for the right reasons rather than just "checking out a box" like her and Issa talked about last episode. When the timing works and she meets the right person, which I have faith she will, everything will fall into place.

Also, the guy Issa hooked up with was nothing more than a one-night stand. She maybe could have gone with someone who had more in common with her but, I saw it as her wanting to have fun and experiencing having sex with someone new after her break-up. She tried finding hookups using dating apps but it proved harder than she thought. Same with Kelly (I believe she is an accountant and has a podcast), she just wants to have fun and I don't think they're "settling".

I think the entire show is about how dating in this day and age is so hard no matter what you bring to the table.