Poles fill up with water when it rains and rust from the inside out.
I've had to replace dozens in my 8 years that snapped from the rust and high winds.
If concrete isn't poured down below the frost line, over time, it will force it's way up. In some places, the Frost line is 5'+. No tech has the ability to dig that deep and the poles are only 6-7' tall.
Poles are the most damaged mounts. People hit them with their lawnmowers, kids hang off of them, or they get bumped into and Dish spends a lot of money to go out and repair/replace them
We don't use concrete anymore, we use expanding foam which costs more than concrete.
Also, the poles we use HAVE a flat spot in them and the 2 trips you mentioned are also wrong. On the first trip, the dish goes on a temp-mount,. The 2nd trip is to allow Dig Safe/Julie to mark the ground and then the pole gets set and the cable buried. Which again, costs more money for a 2nd Truck roll.
The distance from the house has nothing to do with grounding. BUT, Dish only buries 50' for free. After that, it's a dollar a foot in $50.00 increments. so a 51' Cable Trench is $50.00. 101' Trench is $100.00
Also, we don't use Silicone, we use Bishop's tape or Pitch-Patch which bonds with the asphalt and why we can only do roof mounts to asphalt shingles. Try and take a dish off a roof that was properly sealed after a few months and the shingles are coming with it, so no, when it's done right, they don't "make enough of a crack that water is allowed to enter".
Where there is an issue is improper mounting. Not using a roof joist to anchor the dish, not sealed properly and not tightened down although you are right about wind. What happens is the force of the wind, when not secured properly, weakens the wood and the lags will start to pull out and THAT'S where water gets in or the dish starts to "move" weakening it more over time.
And your statement " So why do installers do roof mounts? Because it's not their house and they just don't care, but also because by the time the damage becomes apparent to the homeowner they will most likely be long gone, either retired or in some other line of work." is just ignorant. Unless you work in an industry where people typically "just don't care".
Poles don't fill up with water if the ends are covered. If it's a Ku dish or a Dish/Direct stle dish then a galvanized cap on the end, if it's a C-band dish that typically covers the hole. I've got close to a dozen dishes on metal poles, some of which are way older than 8 years and have never had one snap, including the ones mounted on pipes that were rusty when I got them (I wirebrushed ther surface rust and painted with Rust Destroyer but the inside was still rusty, but still none of those poles have snapped). Perhaps you live near the ocean where the salt in the air corrodes metal? Anyway if Dish doesn't cap the pole ends then that is definitely going to be a problem.
I will grant that there is nothing you can do about human carelessness. I don't have small kids anymore and I don't have the kind of yard that has to be mowed (I live in the country, literally in the woods). But a nice ring of concrete around the bottom of the pole avoids the need to try to get right up next to the pole with the mower. But then I am careful around my dishes, but I have some neighbors that I know would not be so I can see your point there.
I'm aware of the expanding foam option but never used it because it was more expensive. It's also used for setting fence posts but concrete is cheaper around here, only about $2 a bag when on sale. Of course if you are paying for labor then that could make the foam option less expensive, since it's much quicker.
I mentioned the distance only because if you can get closer to the house ground you have to use less wire to reach it, also you don't have to do what some installers do which is run a wire along the outside of the house for a long distance. I don't think dishes are ugly but I definitely think that long lengths of wire running along the siding are. My comments there had nothing to do with what Dish charges for the trench; personally I would always do a self-install anyway or at least pre-dig the trench myself.
Don't assume that the way you do things is the way all installers do things. You sound like you actually care enough to try to make the roof mount secure against the forces of nature, what I question is what happens over time. And then there is always the question of what do you do when it is time to re-shingle the roof, which with asphalt shingles always happens sooner or later (I prefer a metal roof for that reason, but again I don't live neat the ocean). Do you remove the dish, and if you do, will the roofers use the same level of care when putting it back? Will they use the same holes or just make a few more? And then will the dish still be aimed properly or is that going to require another service call (unless the homeowner actually knows how to re-aim their dish)?
Your last paragraph really gets me. Let's assume for a moment that you are the best installer in the country and you do everything 100% right. Do you really mean to tell me that you have never encountered a really boneheaded installation put on a roof by another installer? Nothing that was improperly sealed? Nothing where the lag bolts only went into plywood? Nothing where the cables were routed in such a way that they were pretty much guaranteed to be damaged by ice? Or where the dish itself was positioned right where ice jams would form? No instances of the cables being stapled to the roof, with no attempt to seal around the holes made by the staples? Because I am not a Dish installer and yet I have seen all those things. I have also seen Dishes placed where it should have been obvious that a few years of tree growth was going to interfere with the signal. I don't deny there are true professionals that try to do a good job, but in my opinion there are just as many who see dish installs as a way to make a quick buck, and those guys really don't care because it is not their house (or maybe they are just plain incompetent).
And no, I am not saying that is a problem confined to Dish installers. I've see crappy and ugly cable TV installs. I've seen licensed electricians do things that they knew was against code because they thought it was easier and they hoped that the electrical inspector wouldn't notice, and you should hear them cuss when they have to do it over. I've seen concrete contractors pour concrete pads next to a home in such a way that the rain water runs toward the house. I've seen an asphalt contracter put in a driveway that was nowhere near straight, despite the homeowner standing there an explicitly telling the guy he wanted the driveway to be straight (and also it was not level, so if you park a car in certain spots there is a definite slant to the left). I've even seen contractors just abandon a job midway for reasons known only to themselves. Maybe it has to do with where I live, but around these parts it seems like about half the contractors and professionals just don't give a flying f*** about the quality of their work. And my point is that if it's MY home, I would not be willing to roll the dice and just hope I get a guy like you rather than a guy who just wants to do the job in the easiest possible way and/or in the way that makes him the most money. At least with a pole mount, if they do it wrong it's not going to cause your roof to leak.
(Also if you seriously doubt there are terrible contractors out there, watch a few episodes of any of the TV series that feature Mike Holmes. The days when you can blindly trust a "professional" are long gone, IMHO).