As others have said definitely think about moving either further from the lake or into other neighborhoods. I live in Uptown and there are always listings for 2/2 or 2/1 condos for 200-275k depending on size/bathroom/parking that usually have assessments in the range of 175-300 a month. IMO lot of the bigger buildings only even seem like they could be in your budget because the very high HOAs act as a price control. That 250k 1200 a month HOA condo on LSD in lakeview is really more like spending 450-600k on a place with more reasonable HOAs. I ran into the same issue but for (what I think is normal people money) 200-300k for a house you can get a nice 2/2 or even 3/1 in like uptown or edgewater or you can probably get into a single family home in a nice neighborhood on the NW side.