Server clients can't browse internet . Exchange clients on outlook Can't send external . Certificate issue! Please help!!

SBS 2011 Environment running exchange 2010   SP3.   CiscoRv82 i believe is model (8 port vpn router)    Background info.  Server was migrated from a SBS 2008 box that was just too slow.  Migration pretty much went as successful as I could hope from a wizard.   Folder redirection was broke but Exchange for the most part moved over without issue.  

About 2 months after the migration everything just halts.  

Computers can browse to Google and a few other random sites but mostly just get a certificate error pointing back to my own server along with the IIS7 splash page.   I realized no matter what domain I type, if I put /owa at the end of it, it will load my web app page.   DNS however does resolve in NSlookup regardless of what site I try.    I.E.   I can go to www.nba.com/owa and the server redirects to localhost/owa.     The certificate error pretty much says certificate from remote.mysever.com is untrusted.  

I should note to rule out DNS issues i can ping anywhere externally via ip and dns name.  

Also Outlook is able to receive emails but is not able to send.  It keeps telling me my remote server is rejecting the message from being delivered.   Error is remote.(domain).com #550 5.7.1 Unable to relay ##    I've tried reissuing self cert to no avail.   Outlook acts so broken now it crashes unless I open outlook with /safe parameter.  


I'm wondering if maybe some IIS bindings / certificates got messed up and that's why its redirecting me there every time but I have literally went and reset them a billion times to the point where I just keep fixing and rebreaking OWA etc.   Tried Fix My network WIzard a billion times.