I’ve got a client who needs this setup but I may not be able to get out to him. If I connect to his machine remotely using connectwise, will I have any trouble installing and setting up Tailscale?
There shouldn’t be any problems, at least not because of something between Connectwise and Tailscale.
From what I’ve seen, Connectwise doesn’t seem to clash with any ports Tailscale might use, so you should be good. 