I need to replace the roof on my three flat rental building in Chicago and I'm looking for a roofer that I can rely on for good work at a fair price.  Also, what are some of the main points that should be considered when searching out a roofer (what to look for & ask, square foot rate expectations, etc.)?  Also, any recommendations of any roofers that anyone has worked with in the past would be helpful.  I am not planning to get the job done until spring 2015 at the earliest but think that getting it scheduled now is important.

Its not what they tell to , you will get 3 estimates , each one different . What you can do is write up a bid sheet describing the work to be done , type of materials and the warranty , have everyone bid off your specs .  Check for insurance , and licenses etc.

where in Chicago? specific neighborhood?  flat or shingles?

the most important consideration when it comes to roofing work is work comp insurance.  most investors do not know this, but if you hire a company to do work at your job site, and someone is injured and does not have work comp insurance, YOU are responsible for their injuries.  this happened to an investor friend of mine in illinois.  he hired a roofing company to do a replacement, and one of the roofers fell off the roof and was permanently paralyzed.  the company he hired did not have work comp insurance, so he was sued by a personal injury lawyer representing the injured worker.  

most roofing companies (really most contracting companies) do not carry work comp because it is very expensive and adds a pretty significant cost to each job and is not required by the city to be licensed-only liability insurance is required.  

make sure you consult your atty on this to develop the best plan of action to address this reality.  

I used Angie's List to get quotes from 3 roofers to get a sense of the costs and detailed job description just to familiarize myself with the steps needed to replace my roof and get a sense of the costs.  I think that was the best way to:

a. vet and find a quality roofer 

b. learn about roofing in general (the conversations and quotes helped me research online)

c. ensure I'm getting a fair price

Also vendors care about feedback from Angie's List unlike contractors I've found on my own that would not return calls after paying them.

I was happy with the contractor I used last year and am happy to refer you, just PM me.

Thanks for the feedback from everyone.  It gives me a lot to consider and research.  Time for me to do some homework.

I'll second the statement about making sure the sub has proper insurance coverage including work comp.  Work comp is expensive for a roofer because their industry has historically high claim rates.

In addition, make sure to get hourly labor rates for labor plus agreed markup on materials for items over and above your bid.  When doing a re-roof, you will typically run into something that will require additional labor that wasn't included in the bid - ie replace rotten sheathing.  It's in your best interest to have terms worked out ahead of entering into a contract.

I agree with Rob.  Also get as many bids as you can to bid the job.  I am sure they will all be very different in price.  Good thing about roofers is you don't have to be there to let them in so they can give you a price.  Get the hr labor rate and then what warranty the company gives on their work.  If a shingle blows off in a few months or a leak happens on first rain you want them to come fix it at no cost to you.

Good luck!

Jay,

Flat roofs in Chicago have many problems as you may know. Your best bet is to go with a light commercial style roof. My suggestion is to avoid a TPO and look at quotes for a full or partial EDPM membrane (Well worth the money compared to a TPO and will last much longer). Also see if the roofer can come up with a way to drain it well

First having your contractor have insurance is important.  Second you are not responsible for all medical costs if your sub does not have insurance.  They must show your breached a duty owed to them and were harmed because of your breach.  Now you can be sued anytime for any reason, but there has to be a recognized basis for them to get money from you.  You should ask around for references as well.  Do not just go with the lowest bid.  Make sure they have experience on the type of roof you have as well.  Good luck

roof is nothing to play with. its a costly repair . make sure you go with a reputable company that's being many years in business because you need someone to back up their work. reputable companies are usually not cheaper but you sleep better when you know someone is there when you need them also they provide you with the manufacturers warranty.