Get in at least 3 contractors, general or specialized to the particular 'fix', and see what they say about how they'll approach each job, how long it'll all take, how much they'll charge (and how much they'll want upfront - if anything - for materials), and whether they have references you can call. Make your decision on various factors, not necessarily just the lowest price.

I would also ask what their clean-up/removal procedure is. Make certain that your agreement includes them hauling away old materials and thoroughly cleaning your property of all debris and work materials. Make sure that any fees you'll be charged for disposal are disclosed up front.

Janet

Join Angies List. It's worth the money.

I'd tackle this as siding and windows this year and then the other projects in the future. I doubt you'll get firm prices for the roof now - most estimates are good for only a fairly short period.

Replacing the bottom 2 rows of siding - assuming you have real wood, replace with cedar. It's the longest lasting. If you have Hardie Planking or another composite, stay with it, but make sure the contractor is a Hardie installer. Do you need siding around that 2nd story window if you stay with the existing window? If so, same thoughts.

However, do you want to go back to the larger size window? Do you want the new window to match other existing windows? If you go with a larger, you're going to need to know if a large enough header is still in the wall, but that won't become clear until the wall is opened for the window. Depending on what you decide, ask if the contractor is a certified installer for that type of window - Marvin's warranty gets questionable if a non-Marvin installer does the work. Price the windows on your own so that you'll have an idea of markup when quotes come in.

Do you have landscaping around your house that will be impacted by this work? You're going to need to consider that. Unless you move plantings, they're going to get damaged or killed. Or could you have the work done say in March, before things start growing?

I agree with the disposal questions. I agree with joining Angie's List to get referrals of contractors. I agree with talking to at least 3, but preferably 5.

March is exACTly when plants are about to 'pop' - late fall or winter is the time to move conifers, and deciduous plants should be moved in March, but before work starts.

Everything is still underground in my neighborhood in March. My point is - choose a time depending on your climate. Move plants when appropriate, too.

Thanks everyone for the great advice! I am going to make a checksheet that contains all these questions and considerations. We actually joined Angie's list a couple months after we started looking for a house, when we realized that EVERY house we looked at needed at least 1 major fix. I think we have 4 or 5 people picked out, 2 have been called so far.

DH says old larger window is nowhere to be found, so I think for money reasons we'll have to stick with the little window and side in around it and the bottom of the house for this year. I'm interested to get the roofing price anyway, just so I can start to get a feel for how much a roof costs! It's extremely common here (maybe everywhere?) for 1 company to do both roof and siding and maybe windows too, so I figure they may as well give me a quote while they are there. Maybe I'll just throw it on the credit card to have it done and not do anything else for awhile ;) It's really the most important thing anyway.

We can't really match the windows. Most of them are original double hung wood w/out dividers in decent shape, except front living room window and the upstairs windows are vinyl or something. Eventually I'd like them all to be wood, but that is far in the future.

No, not real wood siding. To me it looks like cheap junk composite, but according to neighbors when it was put on (20 years ago???) it was top of the line. DH is most interested in getting the most durable composite available.

I hate the little landscaping that is there, so no worries on that count!

One little tip that I have used......... when I had a roof estimate done, I talked to my insurance man and asked him who he recommended. And then I called the wholesale roofing supplier --spoke to a secretary and asked who she would use.

First of all, the secretary knows who pays their bills, who has fewest complaints, who does the most work from referrals. They also will talk to you where the salesmen might just hand you some names.

It worked great for me and I have since done with great success with floor covering installers.

Cathy

Oh! Neat advice, thanks!!

This might sound silly, but I found it really helped to be courteous and NICE to contractors... a smile goes a long way at that initial meeting. Most of them want to do a good job and make you happy.

Also, type up a list of project details and give it to each contractor you meet with. For example, if you want them to remove all debris, say "remove all debris." That way, you can be sure the bids you're comparing are for the same work. Contractors aren't always great at taking notes (they've got other stuff on their minds), and are usually happy to get a written list of your expectations.

And if (for example) the first contractor you talk to says a beam is rotten and needs replacing, don't hesitate to ask the second contractor for his opinion on the beam. He/she might have a different solution.

Every estimate you get will teach you something. You can get an excellent education by talking to experienced contractors.

Best of luck with your projects!