I hope you've been successful! 

He's had two successful flips so far and after this third one he's looking to pay off the HELOC and roll the profits into his future flips.

You can ask for whatever you want in a negotiation. 

There are a lot of variables to consider so it's impossible to say if investing in one of those other markets would have been "better".However, I think you could make a stronger case that you have been (or would be) more successful with your real estate investing in Chicago compared to other markets.

But I appreciate that those who have found their footing in real estate and are doing it successfully want us newbies to understand it takes work and at least some capital.

And IMO that has been decades in the making.I saw a recent survey of 4000 Gen Z and they said thay would need to earn 270k to feel financially successful.

I know this post is old but wondering if you found success.

If you are going to add value to the house you might be able to get an equity line against the property to use to fix up the property or negotiate some repair money from the seller that you get at closing.

A seller may direct an agent to negotiate on their behalf within certain parameters or they may discuss how to present/frame a specific response to an offer.

Determine the attributes of experience, knowledge, and capital needed to be successful, and evaluate how you stack up 4.