1. Redo your coil calcs. Why are you using such a large coil? Your first one is more reasonable. 1.22uH needs 28pF to resonate at 27MHz, and you will likely have 5-10pF of strays / circuit loading. C2 = 5uF will kill any oscillation.
2. Use bigger decoupling caps, 150pF has a reactance of 39 ohms at 27MHz. It's not doing much. Use 10n or so.
3. Tidy up the wiring around the oscillator, I have highlighted the wires carrying significant RF that need to be kept short:

I have highlighted both decoupling caps at the collector of Q1 as one is 150p, however a single 10n to ground close to Q1 and with short leads would be fine. You don't need C2 to stretch across the coil, soldering one end of the coil to the ground plane, and C2 with short leads at the other end to the ground plane is better.
This may give you some ideas as to how to keep your leads short:

Good luck.
2. Use bigger decoupling caps, 150pF has a reactance of 39 ohms at 27MHz. It's not doing much. Use 10n or so.
3. Tidy up the wiring around the oscillator, I have highlighted the wires carrying significant RF that need to be kept short:

I have highlighted both decoupling caps at the collector of Q1 as one is 150p, however a single 10n to ground close to Q1 and with short leads would be fine. You don't need C2 to stretch across the coil, soldering one end of the coil to the ground plane, and C2 with short leads at the other end to the ground plane is better.
This may give you some ideas as to how to keep your leads short:

Good luck.
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