What are some red flags?

1950 Single Family House 2br/1ba (there is an extra akwar room that i will make into another bdrm (see pictures)the square footage says 1384, however I believe its a little more because of a laundry room add-on about 10'X8'A new roof is a MUST but there isn't any leaks yet, just a lot of visible patches. 

I know for a fact after having been in this business for a number of years and a couple of cycles that when the market is red-hot, contractors do jack up their prices, stand you up and are just all around unprofessional.

You need to check the building code, because most jurisdictions have limitations on what a minimum square footage for livability may be.

@Jeremy Mattson the main red flag I see is the rehab budget of $85k.

The Millionaire Real Estate Agent - by Gary Keller (The Red Book)The Millionaire Real Estate Investor - by Gary Keller (The Blue Book)I wish you the best on your real estate career! 

I agree with this 100%Zoning restrictions and all the red tape doesn’t make things any better.towns/cities need to ease up 

If you watch a drywall video, then go get a square (you can buy smaller ones at the big boxes) and practice what was demonstrated. 

I believe this will increase my home's value by adding 2 additional rooms and square footage along with a full kitchen and I'll be able to live in the basement while renting out the top floor. 

Chicago, born and raised, currently reside in the in Lincoln Square area.