Saylor - nms, too girly
Holmes - it's ok, nms
Winsor - yes, but spelled Windsor
Tige or Tigue (Tiger spelled in French is without the r) - this is cute
Sawyer or Sayer - Sawyer is great
River - no
Dallas - no, too many female strippers and porn stars named this
Phoenix - no
Parker - too overdone
Hawke - ok, but maybe a little ostentatious
Hutton - don't like
Trenton - not so much
Yaegar - no way, sounds like Jaeger, the alcohol that makes college students go crazy!
Ocean - maybe, as a middle name
Indigo - not good, and definitely not for a boy
Ranger - don't like

I like Tigue and Sawyer.

How about...

Elan (means tree)
Oren (means pine tree)
Asher and Ash/e (Ash tree)
Bear
Wolf
Linden (also a tree)
Rock
Zeev/Ze'ev (means wolf)
Adam - means earth
Green/e
North
Blue
Forest/Forrest
Red
Leaf/Lief
Beecher
August
Clay
Cliff
Bay
Grove/r
Lake/n
Stone
Winter
March
Ridge

The only name i really like out off your list is Parker. The rest are just okay.

Personally i dont like many of the names on your list so i've judged each name on who i think it works with Drake and Hudson.

Saylor - Hate it
Holmes - not a fan
Winsor - Not really
Tige or Tigue (Tiger spelled in French is without the r) - Really no
Sawyer or Sayer - Like it
River - its ok
Dallas - no really
Phoenix - ok
Parker - like it
Hawke - like it
Hutton - Perfer Sutton
Trenton - good
Yaegar - HATE IT
Ocean - not a fan at all
Indigo - No
Ranger - Kinda has some charm

Other suggestions
Winston
Ajax
Magnus
Kaide
Ryker
Cannon
Walker
Garrison
Tucker
Colt

I think with Drake and Hudson (Zoe) you need a really strong boys name. I actually like Cannon, Ryker or Ajax to go with those names best. Off your list i would go for Sawyer or Phoenix. Good luck.