Some people have reported having cashapp accounts frozen by sending chips directly to gambling sites, and there are people who have said it has happened to them on seals.
As far as purchasing from the chat, as I said, there are several trustworthy people in there. Normally you would send via Paypal or on of the cashapp type services and then get chips. Players such as pman, JamieGold and TheCaretaker sell chips there regularly and have never stiffed anyone.
Obviously there are scammers there too, and while the chat community can be somewhat 'raw' at times we try to warn noobs about them. Just gives people another option.
I always wonder, fees are at a low for months now so it shouldn't be that hard to just by bitcoin (or even other crypto). Why taking the risk of using something like cashapp and getting you account banned or using the tipping feature and possibly getting scammed if you use to deal with players that are not trusted. It's so easy these days to buy crypto, honestly.
Maybe it depends where you are. I'm in Australia, and the site I use to purchase bitcoin has a 200 chip (0.0002 btc) withdrawal fee for transfers. So yes the network fee is low but exchange fees are often not.
If someone wants to buy 100 chips (about $12 of btc) to try out the site, is there a way to do that without it getting chewed up in fees?
It's small amounts like that that I am talking about for chat purchases. Obv if you're buying $1k or more fees are less of an issue. YMMV.