Brock Brock Brock Brock

1. How bad of a sign is it that HHH got the upper hand against Lesnar on RAW after Lesnar had been off TV for so long?

It's not a GOOD sign, but I don't think you can read anything into it.  
 

2. If you had to guess, is HHH beating Brock at Summerslam? It's looking like Brock's fate is to be the most expensive jobber in WWE history. Not that he cares, but still.

The only time you can bet on HHH not winning is against Undertaker at Wrestlemania.  And even then, you never know.  Otherwise, I'm pretty sure he's winning.