I've seen the syswatch issue elsewhere before. I may have to try to find out why. When it is installed, it should be enabled and set running automatically.
The WAN IP issue is odd. Someone else had problems getting DHCP leases but it never got resolved. It is probably not related but you may try the version of syswatch in clearos-updates-testing, but syswatch should fire after the lease is obtained. When I had a DHCP cable modem I never had any problems with it in bridge mode so I have no experience of that issue (I did have a different problem .......). Now I have a PPPoE connection.