Kinunir I went through some of the old posts I missed to try to unravel your tale, because although I'm only in my 30s, I'm one of the more old-fashioned ladies on this thread and wanted to give you some insight into how an old-school woman thinks.
I like the man to offer to pay for the first date. It feels chivalrous. However, I will only accept if I want to see him again, because I will then pay for the second. As much as I like the concept of chivalry, I'm not a freeloader.
If actually I really don't want to see him again, I will insist on splitting the bill. If you're on a date with me and I want to go to Dutch, it's a bad sign because it means I don't want to owe you anything because I'm done with you.
Even if you had more money than me, I wouldn't let you pay all the time. I would let you take me to more expensive places and I would reciprocate with less expensive ones, but there would be a clear financial reciprocity. There's wanting that feeling of being looked after, and there's allowing yourself to be bought.
I don't do casual sex - I have to know the man first. I can't tell you how long that takes, because I'm not crazy enough to have an arbitrary rule of something like 2 years. With someone from OLD, it will take me longer to trust the man than with someone from real life, because I'm starting with a background knowledge of zero. It will take longer than the 3 dates most men seem prepared to wait, which for me is turning out to be a really good way of filtering out douchebags. I meet some men who seem utterly charming and turn downright horrid when it transpires I'm not going to sleep with them on their terms - the mask falls.
As someone who doesn't want to fall into bed with a new man straight away, I wouldn't agree to go away for the weekend. To me, that's giving the wrong signal. In an established relationship, I love mini breaks - it's a weekend of exploring a different city and having lots of sex. Weekends away were invented for sex. If you don't want sex yet, you don't put yourself in that position. Well, unless you want a free holiday.
And speaking of free holidays, no woman would take an all-expenses paid trip to a foreign company with a suitor she didn't trust enough to sleep with and not have access to a stash of money in case it all went pear shaped. Frankly, even if she head over heels in love with you and shagging you on the hour every hour, she would still have a backup plan. Just as women cannot be separated from their handbags, we always know where the exits are. In the context of travel, that means passport and credit card.
It's not that she wants to wait per se - there's nothing with waiting. It's just that with all the other background you've given, it doesn't sound like she wants to wait for you. She sounds like in her experience, she can milk a man for money for 2 years before he twigs and she has to move onto the next one.