I've been living in the ugliest house on my street. About 20yrs ago my DH and i bought a handy mans special. Well it didn't take long to find out that my man's not handy, just ~ special~ lol. I'm no better that's for sure. We never could scrape up enough to hire anyone til now.
Hurricane Sandy ripped of pieces of every thing but thankful the only things damaged can be replaced.
It's been no picnic here but so many suffered so much more.
OK back to the good news, So the insurance paid up.
I called a few contractors and OMG what a weird experience that was.
3 contractors showed up and never even got back to me with an estimate! Sears gave me a price that was 3X's the estimate of a local guy. The guy from sears went on and on about this awesome roofing shingle that they charge $26000.00 to do my roof. LOL I didn't get anywhere near that from my insurance. The local guy uses the exact same shingles for $9200.00. Needless to say we hired the local guy. He said when times were lean he used to work for sears and they pay their worker peanuts, and rip off the customer
He's been in the roofing siding business for 30+ years.

I ordered the roof. I'm getting the IKO cambridge dual brown. YEAY!!! lol it took me about 5 minutes to pick and no regrets yet. Now of course the contractor hasn't started yet. My problem is the siding. My place has, well, what's left of cedar shakes siding and a black roof. We decided to go vinyl, cause vinyl is final. And as mentioned neither of us are handy.
I'm really leaning towards sage with white trim and brick face over the ugly foundation. Maybe some red shutters. I'd post pics but photo bucket wont let me log in.
I'm putting a link on to another post I made so hopefully you can see my house.
Any and all input is truly appreciated.
:) Laura

I'm not very helpful, am I? :)

Since vinyl IS final, and the post you linked to is about reworking your garden nonstop, you might want to do the vinyl in a color that is more timeless and do the trim and shutters in the interesting colors that can be changed more easily over the years. I'd just be worried that sage is trendy and might not look good to you in a few years. (If you haven't, ask the home decorating forum. They do colors.)

About 5 yrs ago I bought a new fridge and black was all the rage. I almost got black but got a flash of my mother's old avocado green fridge and chose white. White fridges never go out of style. White houses either but I can't see this place being white or a light color.

I'm heading to the decorating forum. lol I need help.
:) Laura

The financing can't hurt.

I wonder if going through some place like Sears would get your job moved up on the list when you're in a location where everyone needs a new roof due to a storm.