I see your point and I haven't got the time (nor inclination) to do this kind of punting myself but I can imagine it's like fishing (I don't do that either). It's as much about the process leading up to the catch as the catch itself. I would see it as a bit of fun to break up the routine of regular punting.
Interesting thread. Never noticed until it was bumped.
Very much agree with Fuzzy.
But I do have plenty of time to spare and yes it is fun for me to try Craigslist from time to time.
I also agree the site is rubbish now and was definitely a lot better a while back.
I’ve had success though. Placing ads and also answering them.
The time wasting shit you just have to put up with and treat it as part of the game.
Met a thirty something married woman through the site. Initially it was just a chance to lick pussy and get a hand job for a few quid. But we ended up seeing each other for over two years and had some weekends away together. I picked up the bill of course but no charge for anything else. She even bought me a nice gift in me birthday.
Then somebody else came along who she got more out of and our time together ended. Nice while it lasted though.

Also had a few visits to a young mum (Kid at school)
I had placed an ad for amateur models to pose for me and as the OP suggests. Keep chatting and you might move things towards better things.
First visit to see her (her home) I just sat and watched her play with herself. Gave myself a hand job. £40.
But a nice cup of tea and biscuits afterwards.
Saw her half a dozen times and was licking her and having a hand job in the end. Price always the same.
Saw a girl in Brighton too. But always had to book a hotel. Only twice and she was really fit and young.
Only problem was she never seemed interested when in the room. Was a great drinking partner and she ever only wanted fast food so that was inexpensive. But the sex was ………… how can I put it.
Rubber doll shag I suppose…….. although I’ve never shagged a doll……. That’s my story and I’m sticking to it

I still occasionally post on CL. But it’s really hard work nowadays and no success for ages.
But you never know. God loves a trier.
