OS X does support TRIM and you can enable it for all (read: most) SSDs that support it via
TRIM enabler.
I'm not sure if that support extends to external drives. I suppose it could work with an eSATA drive since the system is interacting directly with the drive (well, more directly than Thunderbolt, FireWire or USB).
A quick Google didn't turn up anything definitive, but I think it's safe to say that getting an external ThunderBolt-connected SSD to work with TRIM is not realistic.
As far as reliability, as long as you don't do a huge amount of writes to the SSD, it should be fine. That said, different controllers behave differently; I bought SandForce-based SSDs for my Macs because the SandForce controllers have good garbage collection and tend to keep their performance over time even when TRIM isn't enabled... as long as you don't abuse them.