Valve timing or broken dipstick part?

Does anyone know how much damage can be caused if the valve timing on L series diesel (non intercooled type) is one tooth out? I changed my cambelt a few months ago but was unable to get the timing marks to line up properly after much trying, and needed to get car back on road asap. Its been going, but not great since but today the engine made a bang and lost a lot of power, but it just got me home - albeit slowly. Now in bits with timing belt off and considering replacing cylinder head. It also had a broken dipstick earlier this week, but i wouldn't imagine the broken part of dipstick can get into the engine, it would stay in the sump surely?

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