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Without seeing the erection drawings for your roof, I can say that for my truss roof there were both longitudinal and diagonal braces specified as part of the erection drawing for the trusses. …

Since you are redoing the roof deck, you are at an ideal time to fix this right, or as right as you can without redoing the major framing. … end, or raised at least 6" in the middle and sloping both ways.Cover with ice and water shield (first) and metal flashing in a wide continuous sheet running up both roof slopes. …

With a 1950's house, this would be a good time (since you are re-roofing anyway) to consider adding a "double roof" to address both insulation and ventilation. … From the existing roof deck, that would be 4-6" of rigid foam, 2x4's to make a ventilation channel above the foam, and plywood for a new roof deck, followed by the new roof. …

NAIL holes - not an issue. Larger holes should be patched, unsound plywood should be replaced with sound plywood, etc.

2" deep puddles on a flat roof are a definite problem, and imply at least 16 feet of problem if the minimum 1/8" slope to drain is to be restored/preserved/maintained. … Regardless of process, the entire roof surface needs to slope at least 1/8" per foot towards the drains. No part of the roof should actually be "flat". …

I think standard half-round tiles, if large enough, would be your best bet, other than "having saved all this money on the roof tiles, I can afford to put on the correct ridge tiles, even if it feels like …

in 4 years if it appears to be in good shape now. 25 years is a pretty typical rated life, and your costs for replacement go up a great deal if small leaks you don't notice inside the house cause the roof … decking to rot before you replace the roof. …

0.6° or 1% (1:100 slope) (normally considered "flat" but you need some slope for water to run off) would be "best" for winds (least exposed area to wind pressure) and indeed you'll find plenty of flat …

Far better to both insulate & ventilate the attic better and use "Ice & Water Shield" (a thick, flexible, adhesive underlayer) rather than felt-paper for at least 8-12 feet up from the edge of the roof …

Your roof deck is in good shape, so if you put a roof on it that keeps it dry, I'd expect it to stay that way. … I doubt you are getting hailstones of a size to break your roof deck, or it would be broken, and lacking some reason like that, I don't see much advantage to adding a layer of OSB to support your roof …

It's virtually impossible to get drip edge under the bottom edge of a roof without redoing the whole roof. …

No contractor needed. Cut a piece of 1/2" plywood 3-1/2" X 12", drill 10 screw holes in it, slather it with glue and screw it on there. Might be overkill, but should do the job.

99% of the time there is (or should be) no need to remove snow from a roof that is properly built for the area it is in. … So if your 4.5 inches was solid ice, it would only weigh 23.4 lbs/sqft, well below any standard US roof (minimum 30 PSF per uniform codes even where no snow is expected) …

If you re-roof now, you might not rot out the roof deck and need to replace it as well. … you a new roof. …

Or you may decide that sticking with a trussed roof that does not require central support is the better option, all costs considered. …