If they were in a higher bracket I would spend a bit more time with it though. 

I will also be financing, does not need to be single family, I am open to other properties, such as apartments, but if an apartment, can't spend  more than $140,000 since I am looking to avoid PMI and would like to put down the 25% required to avoid this.

Then they fail there occupancy inspection and end up selling the property for a loss or spending 40K to fix everything.

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.