Thank you Slyfox for the helpful tips. I really appreciate it. I've got a few additional comments/questions if you've got the time:
1. Ice Dam. I think I'm going to pass on this. I saw it at Lowe's today, and you are right - it would cost me close to $200 to add that.
A-1. In my area, there are a couple winters a decade in which we receive the type of weather that ice shield was designed to protect against, in your area those odds are probably less being that you are further south, so like I said, don;t lose any sleep over the decision to not use it.
2. Roof Jacks. Just to clarify, do you think it would be worth the extra cost to leave the first row of roof jacks installed the whole time, and then adding additional jacks higher up, rather than just moving them as needed? My only concern is that it costs close to $20 for each complete set of jacks (two jacks plus one 8' 2x6). I currently have enough for four complete sets. I did pick up a roofing harness today.
A-2. Working from the ladder, tear off the existing shingles four '4' feet high up from the eave, install new drip 'unless your reusing existing' than install a course of felt paper, do that across the entire bottom edge.
Still working from the ladders, install your starter strip and the first three '3' courses of shingles.
Using 16p spikes "Not deck spikes" run one into a stud roughly one inch below the top of the last shingle you installed 'non exposed section',
place your roof jack 'top notch' on that spike than add one more spike in the second to lowest notch on the jack.
When you install your fourth '4'th' shingle the lower 'exposed' section of that course will cover the top of the jacks, so once your done an you hit the jack from the bottom and pound upward until it slides off the spike,
than lift the shingles exposed end to see the spike and pound it down, no roof cement is needed assuming your in a stud like your supposed to be.
You should have roof jacks the full length of the eave before you step on the roof to tear off and they should be left in place until your 100% finished.
You should be able to work roughly eight feet high up off that set than you'll need an additional set of jacks.
Also, with the roof jacks, is it a problem if I need to install them in a spot AFTER laying new shingles? Would I just pound the nails in after I'm finished and cover with roofing cement?
I was thinking that I would begin by scraping the bottom few rows of shingles off, from the ladder, and then installing the bottom row of roof jacks, again from the ladder. Then, once those are on, I could climb on the roof and begin tearing off the rest. I would have to remove the jacks to lay the first sheet of tar paper, then put the jacks back on so I could lay paper on the rest of the roof. Then I'd have to remove them again to lay the first row of shingles, and install them once more to install the rest of the shingles. Does that sound right to you, or am I doing it backwards?
3. Starters. I'd prefer to use the dimensionals if I can, because I got them cheap and don't think I can return them to the place where I bought them. So you definitely advise cutting the "dimensional" part off, rather than just placing it upside down (with the normally covered up part towards the edge of the roof)? And to clarify the starters on the rake will be laid vertically, rather than horizontally, correct? Also to clarify, the starters are laid with the grit (which normally faces the sky) facing the wood sheathing?
A-3. Turn the dimensional over 'exposed side down' and use a straight blade utility knife to cut the top portion 'that you'll use off', once the shingle is flipped over you will see where the two portions laminated together, follow that line to make your cut.
If you just flip the dimensional over and apply the entire shingle for starter strip purposes the will be a very easily seen hump from the ground,
it won't hurt anything but will be an eyesore.
Starters will be laid with the 'grit' upward just like the field shingles,
and yes, the gable ends 'rakes' will have the starters running up them vertically.
4. Carrying up new shingles. When is the best time to do this? I figured it would be after the tar paper is laid, but my dad said I should bring them up first, before the tearoff, because the tar paper is too slippery. What do you think? Either way, I plan on constructing a hoist/pulley system with a sort of "sled" to ride up the extension ladder and then up to the top of the roof to make the job a bit easier.
A-4. I would suggest loading as you go.
Say you need 8 bundles to go as high as you can reach from the jacks,
all the way from one rake 'gable' to the other, than load 8 bundles at a time.
5. Tarps. The weather this week looks questionable. If I finish the tear off, and either am or am not able to finish laying the tar paper in the same day, would covering with tarps be sufficient if it were to rain that night or the next day? Again, I plan on only working on one side until it is completely finished in order to minimize potential weather problems, etc.
A-5. Tear off a '4' four foot sections at a time, from rake 'gable sides' to rake,
clean and de-nail it, install new felt, than do another strip, again and again until you have torn it all off.
Every time you place that course of felt you will have just a couple inches of exposed deck, which is all you need to rush to cover should it start raining, which you could cover by taking a sheet of felt and lapping under the new and over the existing shingles you haven't torn off yet and temp nailing it in place.
Even if you get the felt down, I would still advise covering with a tarp.
I would not have to do this, but I have been installing roofs since 1979, full time, year round, all seasons and have learned the ins and outs of a proper water tight underlayment and trust me when I say it takes more than just proper laps to achieve that, way more than I could explain here in writing.
I'm sure you're busy, and appreciate the time you're taking to help me. If it makes you feel any better, it took me over an hour to organize my thoughts and write this post alone...