If the concern is that someone could see that you're connecting to Tor, it may be worth it to just use a VPN before connecting. Start the VPN before you start Tor. If you're in a jurisdiction that restricts Tor and/VPN access, that's when bridges start coming in.
Big fan of OnionShare. Makes it super easy to share files quickly and securely. To me, site hosting and chatting is nice, but that's not generally my use case.