How wide are the area's to be watered. Rotary heads are generally used for larger area's and are capable of radius's of around 30-35 feet.
Spray heads are used for shorter radius applications with a max of about 15 feet.
They both have the same approx. amt. of heads so it seems to me that either one contractor is going to be reducing his radius on the rotary heads to fit a narrow area or if the area is indeed wider the other contractor is possibly going to have a hard time with proper coverage with the shorter radius spray heads.
Something seems amiss that one is using rotary heads and the other spray heads and fewer sprays at that.

Ok, I asked the "Option 2" guy and he said he made a mistake on the quote. He meant Rainbird 5000 4" heads for the lawn and proposed the 1800's if I wanted to do the shrubs.

With that in mind, the quotes are very similar. The biggest thing I'm finding conflicting information on is the "winterization" that is required.

Option 1 is telling me that the winter blow-out is required to get all the water out. They do the 1st one free and then charge $75/year to do it after that.

Option 2 is telling me that they offer automatic and manual drain valves to allow for self-draining. That means no blow-outs and they will show me how to do it every winter.

I'm getting conflicting information on weather or not you can get away with NOT blowing out the water before the frost. I live in Chicago and some people are telling me that you absolutely need to do that. But others are telling me that the self-draining options work great. And the company is telling me that's all they do for their installations.

Any thoughts?

Not a fan of self draining or automatic draining. With automatic draining you never really know if it is working properly. They do sometimes get clogged over time.. Also, the backflow device, if outdoors, needs to be properly evacuated of water. Not all homeowners are capable of doing it properly. It can be an expensive repair, so you want to be sure the water is out.
As far as the product selections, they are pretty much equal.

The thing that throws me for a loop though is that there are 3-4 companies in the Chicago area that only install these types of systems and they (appear) to have very good reviews all around.

It makes sense for them to offer the blow-out services because:

1) They can make an extra $80-$100/year per house.
2) It appears to be an accepted practice. Unlike say, an annual furnace inspection which most people don't seem to do.

What I'm saying is that if I were the owner of one of these companies and I was 99% sure the self-draining option would work, I'd still probably recommend blowing it out because I'd make more money and it's better to be safe than sorry.

That's the one thing that I can't figure out.

If option 2 is offering to install the turf plus the shrubs for around the same price as option 1 then option 2 is a better value.