Find a neighborhood you love and a place you love. Forget about appreciation for the next 5 years, at least.
How much space do you need? What do you consider a reasonable price for that space? What factors are important to you in choosing a community?
My own view is to always follow the el train line, so I like Sheridan Park also. This is a part of Uptown on the west side of Broadway, in between Montrose to the south and Lawrence to the north. Two el stops, one on Broadway and one on Wilson. Close to the lake (1/2 mile) and about the same from the Metra train stop at Lawrence and Ravenswood. There has been some gang activity recently but all in all prices are good the citizens are becoming more organized. Check it out, I think this area has many things going for it and sales have fallen off (temporarily in my opinion). I should disclose I own property there.
But I digress. . . Look at West Town, particularly those areas between Kinzie and Chicago Aves, west of Western (Smith Park a.k.a The Patch) and just west of Western Ave between Chicago and Division and North to Fullerton. Edgewater Glen, Magnolia Glen are also noteworthy if you want to be close to the lake. I still think Albany Park and especially Avondale is affordable.
Good luck in your search!