When is the best time to hire a certain kind of contractor?

My husband is a contractor. My sense is that the issue isn't when folks would charge more, but how long you might have to wait for someone to be available. At least where I've lived, I've not heard of contractors charging differently in different seasons.

This would be in Michigan?

Also, the price of materials can change based on things you'd never guess, and that can effect prices more than labor costs. I'd suggest getting a few referrals of good folks from folks you know, or use Angie's List, and talk to some possible contractors and see what they say.

For outside work I've been told by http://ask.metafilter.com/210739/it-aint-no-trick-to-get-rich-quick-if-you-dig-dig-dig-with-a-shovel-or-a-pick that Jan/Feb is the best time to discuss the job/payment even if the work won't be done until spring. The contractor gets some $$ and guaranteed work during a dry spell and you get to be first in line at a discounted price. Not sure how that will help you this year though.

Based on what I've heard from school districts that have to do large construction projects, early in the season when the contractors don't have any work yet is best because they want to guarantee themselves some work. I think that later on, they will be trying to get more money out of work if they already have other work to do. I don't have any experience myself with hiring contractors, but I assume you probably get better prices when there are less competing jobs available. That said, I have no clue how much savings you can expect and whether it's worth it to put off plans.

the (theoretically) less busy months of October and November ...is when the contractors are scrambling like mad to finish up all the projects which have run over schedule before the snow comes. A lot of contractors are underemployed during the winter, so if you have indoor work that needs doing that can be a great time to shop around, but I wouldn't plan any outdoor work for late summer or anytime in autumn.

Mrs. Starseed and I have two not-insignificant home improvement projects we'd like to have done by the end of 2013. It's way too late to game the system this way and still get these projects done on your schedule. Also, the kitchen remodel could require a lot of planning and decision-making, so you should get going on both projects ASAP.

There are definitely advantages (and disadvantages) on large scale construction projects to market timing. This is primarily about companies that keep enough people employed to do millions of dollars in construction per month being willing to take on jobs early at lower profit. They are trading of increased certainty for lower margins. Achieving this at the scale of your small projects will be more difficult. The only strategy that might work is a fully flexible timeline. Can they start when they feel like it and stretch out construction? It may be worth it for a smaller contractor to give you a cut rate for the confidence of having a "fallback" job when there are hold-ups at other sites. That could also be a recipe for high frustration as you watch a job that should take a couple weeks stretch out for months with it being a disaster area in the meantime. If you are willing to wait a year the deck/paver people might be receptive when the snow starts falling to commit to a springtime project at lower rate - again trading profit for the certainty of future income.

I am a landscaping consultant/contractor, and if you called me today with your deck/paver project, it would be at least a week or two before I could even look at the area, and probably mid-June before work started. HOWEVER, if you called me today and asked for a consult, with the thought that the work could be done in the late summer or fall, I would be thrilled, since I would know that I already had a nice job lined up for a slower time :) Oh, and I don't charge more according to season, just fyi. Regarding the kitchen remodel, I think a lot of folks aim toward having these done "in time for the holidays", so now might be a good time to get that done.