I never made any money (cash flow) from this property for the past 8 years except  spending money for different expenses and repairs (due to a bad renter and age of the townhouse).

If you allow him to bid a job instead of by the hour, you might spend a little more, but you will know beforehand how much it will cost and he will have allowed himself a little extra $$$ to allow for variables. 

They'll pass your name on to the buyer (who probably already has his own contractor).If a contractor will agree to run out and spend a few hours on a make-ready estimate for a new investor he's never met, that's actually a red flag about the contractor.Start with the books.

I wouldn't pay the premium to buy one via an auction or some other domain name selling service.Be creative - for example - you could do something like this:WindyCityBuyers.com - OR - WindyCityHouseBuyers.comJ Beard is right that we spend a lot of time trying to adapt to changes in Google's system.  

If you have time consider spending 30 minutes for 30 consecutive days on Bigger Pockets.

You would likely spend more in lawyer fees than you would be able to recover.

It's usually good practice to be overly conservative and to retain excess capital for repairs etc, so I wouldn't go out and spend all of your cash at once.

House hacking would free up what I currently spend on rent and what doesn't go to repairs, would go toward another investment opportunity.

I spend a large portion of my time doing high-level new development analysis.  

We're just hoping to fix this without spending too much time and $$.