Likely not, the thing is that most of the big cloud providers definitely have a networking team and it definitely monitors for bittorrent traffic. The thing is they will monitor but until they get a DMCA you normally don't get popped. However, some providers are more finnicky than others and will disable you immediately if you use 6881 w/o encryption. The key really is not to get a DMCA and not use default ports.
This is true for most providers but not the big big ones. Ask me how I know ;)
You would need to host your own or join a matrix server. The benefit of Matrix is you can tie in puppets to things like iMessage, Discord, FB Messenger if you host it yourself. Another option is Beeper (Matrix + all the puppets for other messaging apps) but you still have to sign up and get an invite from them to join for now.
Lol my dumb self was reading this as WatchOS and then though they meant the Apple VR headset :P
My advice to you will be you should likely look to getting a Developer Account/using a free one from something like AppDB. I am not sure how things will be with sideloading, but services like AppDB have plenty of options sideloading pirated apps. I'm sure that will be updated at some point for wearOS.
The big "but" in all this, is unless it requires you to tie it to an iPhone/Mac, there may not be a way to extract ipa files to sideload.
If you mean WATCHos, then yeah. AppDB sideload to an iphone. Example is like Calcbot 2, you can sideload it to your phone and use the watchos app cause its on your phone.
You need to go to private communities like GGn
If they did have a crack, you'd probably have to disable SIP if it's that good.