My boyfriend's "compliment" made me very uncomfortable

Me and my SO have been together roughly a year and he seems like a nice simple kind of guy. But sometimes stuff comes out of his mouth that makes me wonder how he views women. Usually its benign stuff like feeling like he needs to ask a womans father before marriag. I've been chalking it up to him being slightly more old fashioned, but my ex ended up being quite the misogynist so I'm a little worried.

This most recent comment really bothers me and I'm not sure if I'm over reacting. Me and him and just got done being intimate and were laying in bed. He's all smiley and happy. Then he looks at me and says this:

Him: I'm such a lucky guy.

Me: Oh yeah?

Him: Yeah. I got you and your beautiful and not some crazy ho with four kids.

Me: .....thanks I guess...

Him: What it's true?

Well that killed whatever moment we were having. It made me feel like I was being appraised based on my sexual history/lack there of. I made me feel bad because one of my best friends is a single mom. And it made me feel like he has really shallow views/standards that he holds women to.

My BF is generally really nice. But sometimes he does stuff like this. Or a while ago he was complaining how unfair courts are and child support is because women spend it on stuff beside their kids. Which can happen. Just like men can not pay it by working for cash. He went so far to say there should be special stores for child support money with limited products and have a card to make sure there is no fruad. I'm like why not do it like a food stamps card but accepted everywhere only prohibit alcohol, tobaco, sex toy, and firearm sales. Nope, gotta be a store so people cant let others use the card. Not like kids need denists, sports supplies, field trip money, or anything else normal parents pay for. Men should only fund food and diapers apparently.

Edit: OMG I didn't expect this avalanche of replies.

Edit: A lot of people asking ages. 27 (me) and 29