Q 276 What would you do for the unarmed strike progression is someone wanted to gestalt a monk/swordsage?
Q 277 How do you add reach (preferably a template or feat) to a creature(s) so that they can attack an annoying pest of a pixie ranger/scout who's constantly moving back and forth, and won't get in the range of my melee attacks?
Now for questions that likely are NOT so simple as no one's able to give me a clear cut answer, not even Sean Reynolds, and that's saying something. If you've got answers, I'd love to see the reference material to back it up because I need it.
Q 279 How does a roper's SR of 30 progress as it's HD and CR go up?
A276: Assuming it's an unarmed swordsage, you do the same thing you do whenever you try to progress the same feature twice at the same gestalt level: not much. You can't progress the same class feature more than once at any gestalt level, so your monk//unarmed swordsage would have an unarmed strike progression as per the levels that he took monk, unarmed swordsage, or both (and the levels that he took both don't count twice, even if he takes levels with neither class later on).
A277: Anything that increases size will add reach, such as the Half-Minotaur template. There are a few templates that add natural weapons the specifically have greater reach, but the only one I can think of is Voidmind (and you don't want that one).
As per feats, the Deformity (tall) and Inhuman Reach feats grant you extra reach (note that they both require prerequisite feats). There are a few others that give you reach, but they're more limited or more obscure.
A279: It doesn't. A Roper has an SR of 30, whether it has 10 HD, 100 HD, or 1 HD. If you want to increase it, you'll have to do so manually.