Depends what you are currently paying in rent, how much time you will shave off of your commute, and what your longterm strategy is.

I definitely recommend checking out the podcast- I usually listen on my commute to work.I'm also based out of Buffalo- if the two of you would ever like to meet up for lunch, let me know!

I commute to work right now, which takes me about an hour each way, so I want to be closer.  

Easy to rent because of great school, walking distance to CTA blue line, close to O'hare etc..but property price is high like any other good neighborhood so cash flow will be on lower side...House hacking will work if you run your numbers right...it's nothing but a numbers game.

I want/need some distance between me and them as I have a hard time saying no to requests. 

The hard part is getting there due to commute traffic from Woodland.

I'm currently renting in Fed Hill while working in downtown B'more and the walkability of my commute and everyday life has really grown on me.  

After my move, my work commute went from 10min to 40+min each way.

I'm a new long-distance real estate investor.

I have not heard about Scotts' book yet so I do not know about the benefits of house flipping and how much time it normally takes.My issue is that I am limited on free time as I have long commute to work.