Aside from that, I am very diligent about paying myself first and making all cash savings/investments come before any bill, monthly expense, discretionary spending...etc. 

Obviously there comes a time to do a full replacement (you don't want to risk a major leak/damage to the interior), but if you can spend $500 now and get another 5 years out of the roof as is, that might be a good business decision. 

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. 

Properties that are unique in their neighborhood are notoriously difficult to calculate for accurate investment value.Do you want to be left stranded, committed to buy at a price the Seller already thinks is the best net-price they can get, and you would be gambling it wasn't?

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.  

Similarly, if you're the riverboat gambling type, you can try looking into an equity deal where the buyer pays you X% of final sales price and/or a percentage of rental income if buy & hold.

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.