I love Trout and Kershaw. I would probably go with the notion that they are sure fire hall of famers, but I would have said that same about Dale Murphy or Don Mattingly. I think both are priced accordingly and I don't know that there's that much upside. Modern production further complicates things. To be honest, I think modern cards are relatively limited even in comparison to the 60s or 70s (high numbers being the exception) but people only care about the auto relic.
If it were my money and I wanted to go modern, I think I would buy Bryce Harper. He had an off year because of injury, but there is a reason for his off season. He just turned 24, which is the approximate age of the sweater I am wearing, and already has more than 120 Home Runs and 600 hits. Plus you can get his 500+ deadlift for a fraction of what you can get Trout for.
I have absolutely no problem putting the money into vintage cards, but your ceiling will probably be limited. The buy what you like sentiment is right on.
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