I am aware of some basic goals of a decoupling and grounding layout: Reduce EMI by minimizing overall power-GND high-frequency current loop area, minimize ground inconsistency by reducing impedance to GND connections, keep high frequency current from going to other devices.
These goals have led me to a dilemma between two layouts, both of which I can find support for in previous answers to questions.
Option 1: Only connect a single via to GND plane
Pros: Hi-frequency loop currents are kept off of GND plane.
Cons: IC GND pin to GND plane connection may have too much inductance. Oscillator capacitors may be ineffective due to long distance from GND via.
Advocated here: Competing PCB Crystal layout recommendations Decoupling caps, PCB layout
Option 2: Place GND connections as close as possible to GND pads
Pros: Low-inductance ground plane connection for all caps and the IC.
Cons: According to the above links, this creates a "Center-fed patch antenna" which will radiate EMI and pollute the ground plane with high frequency currents.
Advocated here: Which of these layouts for decoupling capacitors attached to an IC is wrong?
Board details
This is a 4 layer board with internal VDD and GND planes.
IC U1 is the Microchip MCP3425. Y1 is a 20 MHz oscillator. The IC outputs 1Mhz CAN Bus signal and 20 KHz SPI signal.
C1 = 0.01 uF IC bypass cap. C2 = 0.1 uF IC bypass cap. C22 = 10 uF local Feed point decoupling cap. Y1 = crystal oscillator. C8 and C9 = 22pF oscillator caps.
Edit 1
The PCB is currently TOP SIGNAL-GND-5V-SIGNAL BOTTOM, and it is a single sided design, so the bottom signal layer has no components, just routing signals. The TOP signal layer is 1.5mil from the GND plane.
Which layout is more effective for decoupling and grounding?
EDIT 2 Option 3 Here I have incorporated some of the feedback below. Each cap now has its own via to GND plane placed close by. Extra vias are added to lower inductance. The GNDs are all still connected on top to reduce ground bounce.
EDIT 3
OPTION 4
Based on BobFlux's answer with decoupling cap by VDD.
Pros: Decoupling cap is by VDD as expected.
OPTION 5
I'm not sure if putting the decoupling cap next to the GND pin is frowned upon, does anyone have thoughts? I really like how there's only 1 GND via on the IC's power loop, every GND connection has an immediate adjacent via, and al the GND vias are fairly close together so GND plane "Patch antenna" effects should be reduced: