You're complaining about bugs you haven't encountered yet. If the software simply defaulted to working when it couldn't contact a licensing server, would that resolve things?
Having the tool ping a server every week doesn't make the tool any harder to crack, and cracked versions obviously don't ping the server, so there's no reason whatever to be draconian about what happens when the check doesn't go through.
At least that's the approach they took at Adobe. IIRC the tool worked normally for up to a month without pinging the server, and after that showed warnings but kept working for a while. The times may have changed but idea was to err as far as possible on the side of lenience, because anyone using a version that pings the server is by definition a paying customer and not a pirate.
