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Hey, I'm happy to see this question here since it's also a big interest of mine.  Check out the convo here a bit, but note that it's like 3-4 years old now. 

From people I have talked to (instructors and graduates of TPS, members of my squadron, etc.), it is certainly possible for ANG (I think also Reserve, but I specifically only asked about Guard) pilots to go to TPS.  I obviously can't speak to specifics of how it is viewed from a squadron perspective for your squadron, but I know that my squadron had a pilot (a Major) recently leave for Guard-specific role in the test community somewhere in Arizona.  I'm blanking on the name of the program, but it sounded very similar to TPS; I'll post here if I can track down what it was called.  Squadron leadership seemed very supportive of the career move. Best time to do it is totally dependent on your career goals, but noting from the link I provided above, you do transition into an Active Duty role, so keep that in mind.  

I'd definitely be interested to hear what other people have learned about this topic too!

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