Rather than refer to Bucktown (which I'd describe roughly as Ashland to Western and North Avenue to Diversey) I'll refer to census tracts (which s how most Realtor's search the Multiple Listing Service). The area that you're describing as West of Western, I'd probably refer to as Logan Square. However for the sake of this conversation, both Bucktown and Logan Square fall inside the West Town census tract.
Generally speaking the Logan Square part of the census tract will be lower priced than the Bucktown part of the census tract. If you're looking at a 3BR, 2BTH condo with parking, A/C and in-unit laundry, your average price in Logan Square is around 353K right now as opposed to about 488K in the Bucktown section of the census tract. In addition to the pricing differences, there will be a signficant difference in the number of units that are available to buy in each of the area.
If you are planning to buy and hold for quite a while, then you should see appreciation over time in either market area (even assuming a further slip in prices over all of 2009). But if you are planning to resell in just a few years, then you may want to take a harder look at how the "fantastic" place that you found might hold up price-wise compared to similar properties further East. As much as pricing is based on comparable properties that have sold within a certain radius of the property that you are considering, there is always a "perception" factor that can affect pricing as well.
You sound like you have a pretty good handle on the local area and what the appeals (and drawbacks) are for you. Do you think that most folks who are looking to buy in that area are doing so because of the amenities? If so then you may want to be in a resale position where you can more directly compete with units that might have a slight amenities proximity advantage over the one you're describing.
If you need any assistance locating or price-comparing your property to others in the area, then I'd be happy to speak with you. You can contact me directly via any of the information listed below. Good luck.
Broker Associate, Sudler Sotheby's International Realty