Tuckpointing

( sigh )
I have had a murderous time trying to find someone to tuckpoint a small section of our chimney. It is a small section, but near the very top of the structure (approx 25 ft). Throughout the year, no one would return my calls. One guy who did insisted on tearing the chimney down to the roofline and reconstructing from there.
My wife is at the point where she wants me to do it myself with the neighbor's ladder truck, and a caulking gun loaded with a tube of mortar repair. Despite my parasailing adventure when we vacationed in Mex last year, the idea of doing this makes me VERY nervous. Plus I am dubious as to the virtues of Mortar-in-a-Tube and what will keep it from just falling through the joint.
What I want to throw out here is, when should I start to worry about the chimney's structural integrity? I am concerned with a small section of the south side about 1 foot by three feet, with several joints open but most of them looking sound. I would rather try and wait until spring when I might be able to get a pro out here.
BTW, the fireplace involved is used only with a "gas log" and that is very infrequently. No wood fires.
Thanks
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The bricks you see on the outside are not the pieces that keep the fire and smoke in control. The fire and smoke are controlled by flue tile or other actual chimney liner. The bricks are primarily decorative, but if enough moisture comes through the brick veneer, you could develop a ceiling stain or other interior leak. I tell you these things so you don't worry about it so much.
:You can take down the bricks and relay them yourself. You can wait for a better cycle to hire the work done. You can hire or perform having the bricks capped with Hardie siding, stucco, or other suitable material. Have a sheet metal or copper chimney cap made to take the place of the mortar cap, with or without spark arrester, bird screen. Were it mine, I would leave the bricks, cap with Hardie, and install a cap. It sounds as if the original brick work is good enough shape to shed water so the step flashing is still in good shape - keep the siding well up off the roof and don't add fasteners into the flashing.
(top posted for your convenience) ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Keep the whole world singing . . . . DanG (remove the sevens) snipped-for-privacy@7cox.net

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Dont use caulk it will seal in moisture , freezing water will cause damage. Keep looking it is best to have it tuckpointed before winters freeze and thaw cycles.
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