I can take a hint when a chick isn't interested over text (left on read/delivered, doesn't respond back, short choppy replies, etc.) but recently I've been having trouble with if I should still pursue a woman.

I only text the women I go on dates with to set up the date and nothing else. The tone of setting up the date depends on the woman but sometimes it can be warm and welcoming and other times be cold and straight to business. Some will act uninterested over text but really interested in person and vice versa. Some I choose to not pursue because they are a basket of red flags and don't meet my criteria (like this one girl who asked me for rent money the day after our first date). I really don't ever know what's gonna happen and what the other person thinks... that's just dating though.

My main question is when do you know to stop pursuing someone? Do I ask them out twice and let them ask me out for the third date and move on if they don't? Do I move on if they don't even offer to split the bill on the first two dates? How many dates should I ask them out on before I say "she's just not that into you bro" and move on? If they don't show me any IOI on our first 2-3 dates do I say the same thing? I guess I'm overthinking this

My time and money are valuable to me so I would like some of y'all to take me back to the basics and share some cookies of knowledge. Thank You!