I've been making offers, sellers are even accepting the offers but once I do a rehab assessment I go immediately into the negative (bc contractors quote me more than expected) and I am forced to ask the seller to lower the price and we end up in disagreement.

If the score isn't good I'll look at the negative issues on the report and ask questions.

Aside from flood zones, the age and condition of the property, the crime score in the surrounding area, and any potential liabilities will all be things that could negatively impact your insurance premiums.I messaged you the insurance brokers that I work with. 

Just remember: most negative reviews are written by problematic tenants.

Hey @Seb Ko - Negative, Chicago does not require any paper work for rentals over 30+ days. 

There are no barriers to entry (same reason why it appears enticing to you) and there are many negative factors that others mentioned.

I know that its okay to be cash flow negative at first but when analyzing a property I am not sure what a general percentage I should be looking for.

If I refinance and pull a loan of $800,000, the debt service will eat away my cash flow from the current property and I can't find another property that will combine with the current property to cash flow $4k monthly.Basically, if I refinance I will be cash flow negative from my current net income on the property.Is it better not to refinance in my scenario?

Renting out the other rooms in your unit is smart as you'll be CF negative pretty bad if you don't.

By the way, breaking even is negative CF waiting to happen.