Thanks BigMonkey, especially for the siding tips and info - that would be my last project.
You're welcome about the housing market comments!
The roofing guy came today.
The bad news is that he didn't install a flashing, because the chimney never had one, and it would have cost (a lot?) more.
I had maybe slightly misunderstood.
He used Karnack Roofing Cement (red and yellow can) and, for strength, wrapped a "sheet" (can't think of the right term) around it.
The good news is that he fixed several areas of the roof with a bunch of new shingles.
He also put pipe collars around two tubes (both rubber gaskets had deteriorated, in one case an entire piece was missing and the sheeting was nailed down with one nail instead of four.
He also found (small) holes where the siding people (brand new siding done by previous owners) had hooked their scaffold up to the roof for support.
They had plugged two holes but forgotten the other two.
He also spray painted the two pipes and a kitchen exhaust and removed the flag pole and hooked up the chimney cap I bought at Lowes (just a few screws) while he was up there.
He used roofing cement AND netting to hold it better.
He indicated this is temporary (will prevent leaks around chimney for about 2 years and provide the same protection for other areas where he placed new shingles).
He stated that when I get a new roof (about 2 years from now; it is the only old thing remaining on the house luckily) to make sure they install flashing (and counterflashing I guess too).
In other words I, if I am still there, will have a roofing contractor do the entire roof and flashing in one job.
I should also monitor it, especially in spring which is the worst time for rain.
The fact that we had a lot of rain (i.e. some big rain storms) since I moved in last summer with no damage and that he went over the entire roof today and fixed the problem areas, leads me to think I won't have any issues for the next 18 months or so.
If I DO decide to keep the house, I will get the roof done within a year to be safe.
Fortunately since it only has ONE layer of shingles, the new shingles can be applied directly on top, saving the removal costs.
Total estimate about $3,000.
He spent over 2 hours and the price included all materials too.
$440 (no tax) as opposed to $400 due to an extra $40 for the extra pipe collar ($10) and work on that part; he hadn't noticed it yesterday. I am glad he saw it, because it would have been a shame to have all the work done and one small area go unnoticed.
He checked entire roof and fixed the areas that were in need of repair.
He pointed out yesterday how the overlap was far too little and that the chimney taring and semi-flashing (whatever that silver stuff was) was done badly in terms of gaps being left where the water could enter.
He did a great job with GAF tiles and just in time for the snowstorm (6 - 8 inches) tonight and rain tomorrow.
The inside of the house had not suffered any damage, so I am glad I caught it in time.
I should note that the chimney is in the center of the roof, so unlike many house, this needed protection on all 4 sides.
Everything looks much better due to spray painting and him making the
black line on the chimney straight and such that it evenly covered the chimney.
All in all I am very happy (he did everything properly/ thoroughly) and will have peace of mind.
Better to be wise and spend some money now, as opposed to getting major water damage later and ending up with a MUCH bigger bill later - I wouldn't feel comfortable trying to replace all those shingles myself and trying to figure out WHERE (in which spots) they needed replacing in the first place.
Thanks again for all the tips!