Kyle, yeah, it's a pain. And yeah, it's a lot of work. But I think it's worth it. I started roofing with this same thing. Unless the pitch is too steep it's an easy job. I didn't rent any tools; just used my hammer & a garden fork to strip the old roof off. It's a good idea to put drip edge on as well, but that stuff is cheap. You might consider dropping the price and telling the buyers up front that it needs done, too. That'll save you the hassle & be honest to them as well. I kinda like doing these jobs for myself, though. Others may see it differently.
Your mileage may vary.
Don

Don,
Good to know. I have yet to climb up on the roof to see if the pitch is manageable, so that will probably govern my decision.

Thanks again,
Kyle

One thing to keep in mind about roof work, which will become achingly apparent once you start, it the amount of lifting of materials involved. They are heavy, and there are alot of them needed, especially if you are replacing the sheathing.

If you have a crew available, maybe it's not that big of a deal, but I found the days got pretty long the year I single-handily replaced my garage shingles!

I completely understand why all the roofers have those ladder-elevators.

It's not a complicated task, but it is a lot of work and heavy lifting, and it can be rewarding to look back on.
The old roofing will weigh about 250 pounds per 100 square foot, per layer (and you have three layers on a roof of 400 to 600 square feet) You should plan how to dispose of the old material before starting the rip-off phase.
Installing new sheathing might be successfully accomplished single-handedly, but I'd opt for a helper or two, just for safety's sake.
The new shingles will also weigh about 250 lbs per 100 square foot, and it comes in 88 lb packs. (The roofing paper is extra.)
I've used a hammer and I've used a compressed-air nail gun. The nail gun is a lot easier, as long as you don't trip over the air hose.

It's not brain work hard, but it most definately is body work hard. If you're at all out of shape, timid around heights, or don't have the vacation time to take off that's flexible to take when the sun is shining, then this job is NOT for you to do.

I'd rather go to work to pay someone else to do it.

And, as a homeowner, I'd rather offer a credit so the new homeowner could pick out their own color and style of new shingles. Heck, make it into a selling point! Get a couple of estimates from roofers for the different grade of shingles, from your basic nothing all the way to high grade architectural. Show the estimates, along with a sample of the shingles when the house is showing. Give a credit for the low amount, but stress that the new homeowner is free to upgrade to a better quality/looking shingle by just adding a few more of their own $$. And they can even pick out their own color then! See, selling feature now, instead of selling drawback. :~)

Live Wire, that's what I call thinkin'! Very good points you've made.
Don

live wire:
I missed two out of three of the "requirements", lol. Yeah, I am coming to the conclusion that maybe a seller credit would be a better idea. Then I can at least give the buyer a choice of how they want to handle it. Maybe they know a roofer, or just want to let it go a while longer. I doesn't leak, and it is barely visible from the road, so it may not be a priority to someone else, as it would be for me.

Thanks again for all the great input,
Kyle

I agree on getting someone else to do it. From my experience a credit at closing is good, but what seems to work even better is to have the estimates in hand and have the broker tell the Buyers that they will receive a Bank Check at the closing for the amount of the estimate. They may think that they can do it themselves and save some money, but what do you care. Anyway, the bank check seems to have more impact on people than a credit.

I don't agree with the credit thing. When you sell a house you want to minimize visual negatives. It usually translates to lower offers. Now they have to go through the effort of having the roof repaired, not you.
Why is the garage roof so bad? Isn't the house roof the same age and construction? Or was it that when the house roof was done, the garage roof was put on hold?
Put a new roof on the garage that matches the house. The fewer issues that arise on the house showing, the better. Especially if the market is slow.
Ron

The big benefit of including the roof job as part of the house deal is that you need no cash up front. If the garage is not terrible looking now, it might be a good way to go. On the other hand, if the roof looks really bad now, it might make the buyer think that there is serious water damage under the roofing and it could scare them off. Nobody wants to repair a roof that has compromised lumber underneath - that could lead to a big and expensive job.

You might want to go with a compromise: Tear off and possibly redeck the roof yourself (with some help). Then, hire a roofer to finish. You could probably cut the cost in half.

The tear off will not be done that much faster by a pro than yourself so you save a lot here. The roofing (and perhaps the new deck), however, can be done in less than half the time by a pro, and it will be done right and looking good. And, by the time you finish with the tear off, you will probably be ready to step aside and let someone else take over. Shingling a roof is tedious, done with a hammer and nails, and it is very easy to goof up and put the shingles on a bit crooked if you don't know what you are doing. And you can tell the new owner that the roof was professionally installed if you hire out for the shingling.