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I have used alias forwarding (to Gmail) as a mechanism for disaster backup in case Fastmail becomes unavailable (as happened recently as a result of a DDoS attack). I am unaware of any delivery issues. However, all the backed up messages go to the same Gmail account, and some messages could be silently discarded, or placed in the Junk folder without me noticing. In general, after initial testing, the only time I access the backup account is when there is a problem at Fastmail.
It seems likely, to me, that Google would learn to trust messages going from Fastmail to specific Gmail accounts on a regular basis. No guarantees.
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