I kick myself realizing if we would've sold a couple months later we probably could've made 10-20% more on it.

I personally prefer public REITs. 

I can build a brand new home cheaper and bigger than what I can buy used- far more equity in new construction than in remodel/repair... but again that's doing most everything myself with a small crew and a couple of subs.My mentor builds spec homes and 2-4 unit MF.

I started a nonprofit we'd prefer a premium finance loan.

Also, I have a couple of other properties as well.  

Obviously a good deal and better starting position would be preferable, but in my area and timeline I feel it could work even for a pretty average purchase. 

Cash flow may not be great in the first couple of years so it depends on what your goals are.

I think you are probably priced right if it were summer, but may need to drop another $100 given the Chicago winter.Most important if you are confident in your price it is often just a timing thing...the right tenant will come, but I know it's tough when you only have a couple of doors...that lost rent hurts.

I'm currently developing a 4 family townhome in Cobble Hill Brooklyn, and have a couple friends doing various projects similar to yours in Park Slope(where I also live).  

I own(ed) a couple condos in the city and want to expand my real estate portfolio as I do not see the growth of the city slowing down at all.