I came across a two-flat on Winnemac Park in Ravenswood that I think is a terrific deal. Solid building, updated mecahnicals (including partially finished basement with individual furnace, move-in quality two bedroom units, great yard, deck... right on Winnemac Park.
I want to buy the building for myself. But with a kid on the way, my wife is just not up for squeezing four of us in a two bedroom (while using the basement too). We also finished our current home and moved in while expecting our first kid... and barely made it before he showed up. Just not the right timing for us.
However, even if you are looking at condos or town homes in the $350,000 to $400,000 range, you should also check out the numbers on this move in two-flat. It could probably sell in the $425,000 range. With only 10% down and using conservative numbers...all in, you are looking at $3,500 a month carrying. The rent for the top floor two bedroom with one garage spot should be about $1,100. With a little more money down, you could own a building in this great location for around $2,000 a month (including taxes and insurance and some monthly maintenance factored in).
If you have 20% down, on the $425,000 purchase price, you're looking at a great long term home with numbers that really make sense. You may also just start living in the building as a single family home and slowly convert. I have already brought clients as well... I think its a great opportunity. I would have kept renters upstairs for two or three years and then converted... you may want to duplex down. The basement is ready for a little carpet and dry wall and can be immediately used as a family room + bedroom and has a ton of storage space.
This is not my listing, so please contact me if you're serious about looking into two-flats in the area.