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To make up one's own mind about Wes Montgomery I can only recommend this 4CD box including 8 of his LPs:
http://www.amazon.co.uk/8-Classics-Wes-Montgomery/dp/B005I4ULA2/ref=sr_1_6?s=music&ie=UTF8&qid=1439024130&sr=1-6&keywords=wes+montgomery
Includes: FINGERPICKIN – 1957
THE WES MONTGOMERY TRIO – 1959
THE INCREDIBLE JAZZ GUITAR OF WES MONTGOMERY – 1960
WEST COAST BLUES (with HAROLD LAND) – 1960
MOVIN’ ALONG – 1960
GROOVE YARD (MONTGOMERY BROTHERS) – 1961
SO MUCH GUITAR – 1961
GEORGE SHEARING & THE MONTGOMERY BROTHERS – 1961

For a wider choice of jazz guitarists this 10CD box could do:
http://www.amazon.co.uk/Jazz-Guitar-Ultimate-Collection-Albums/dp/B00IFTU0LM/ref=pd_sim_15_4?ie=UTF8&refRID=1K2VBJM4TRC2RVD32WV1
The complete list of albums included are: Wes Montgomery - 'The Incredible Jazz Guitar of Wes Montgomery', Kenny Burrell - 'Blue Lights Volume 1', Jim Hall - 'Jazz Guitar', Herb Ellis & Jimmy Giuffre - 'Herb Ellis Meets Jimmy Giuffre', Mundell Lowe - 'Guitar Moods', Tal Farlow - 'A Recital By Tal Farlow', Joe Puma - 'East Coast Jazz 3', Jimmy Raney - 'Jimmy Raney featuring Bob Brookmeyer', Howard Roberts - 'Good Pickin's', Freddie Green - 'Mr. Rhythm', Oscar Moore Quartet - 'Oscar Moore Quartet', Django Reinhardt - 'Souvenirs de Django Reinhardt Vol. 1-3', Billy Bauer - 'Plectrist', Charlie Byrd Trio - 'Charlie's Choice', René Thomas - 'René Thomas et son Quintette' and Luiz Bonfa - 'Amor! - The Fabulous Guitar of Luiz Bonfa'.

Both boxes are quite cheap and - in my opinion - worth a try.

Ulrich