I have been reading about the Aleutians, that interesting archipelago West of Alaska where the wind never stops blowing, sometimes at a ludicrous average speed.
This book explains some of the interesting features of Aleutian Islands weather and how to cope with them if you are a pilot...
A number of the airports in the Aleutians exist because of US military activities in the islands, initially during World War II, but later during the Cold War, when US reconnaissance aircraft flew missions to watch Russian missile development and testing activities. Several large airports and their facilities (notably Shemya and Adak) date from that period.
Flying in the Aleutians is a difficult proposition, especially if you have a small airplane, partly because the weather is challenging (for "challenging" read "often downright dangerous").
Here is a sample METAR weather summary for Shemya on 1st December 2008:

PASY 012235Z 03033G45KT 7SM BKN028 OVC032 01/M02 A2982 RMK

The wind report is wind at 030, 33 knots gusting to 45 knots (!). The runway orientation is 10-28, meaning a colossal, gusting crosswind. Not the sort of place to be testing your plane's crosswind limits...

The other factor making flying challenging is that Avgas supplies are extremely limited. In most of the Aleutians, the only piston engine fuel is Mogas. A quick look at the Airnav database entry for Adak, which was a US base in the Aleutians, and is the best airport in the Western Aleutians, shows that Mogas is the only available fuel for piston engines. There is no 100LL available at any airport west of Unalaska (Dutch Harbor). If your plane cannot operate on 87 octane fuel, I suspect that you cannot operate west of that point, unless you can find a source of premium Mogas near an airport.