The most valuable question in any inspection is the one that occurs to you while you are looking at the thing. Not the one you prepared, and not the one that surfaces at nine that evening when the report is a PDF and the inspector is asleep. The one that arrives in the middle, because you can see what they are pointing at and something about it does not add up.
Watching live is the only arrangement that catches those. So it is worth knowing how to raise one, given that you cannot talk back through the page.
Three ways to ask, and when each fits
The question button. If it is switched on, there is a button under the video reading "I have a question about this." Tapping it saves the exact frame you were looking at, and your inspector reviews the saved frames afterwards. A small confirmation appears so you know it worked.
Understand what that button is and is not. It is a bookmark. It sends no text and it does not buzz anybody's phone mid-walk — an inspector twenty feet up does not need a notification. What it produces is a picture, pulled from their own stream at the second you were confused, waiting for them when they come down. That is a far better prompt than "there was a dark patch somewhere on the left side."
Calling up from the yard. If you are on site, this still works and is still the fastest route. They are forty feet away.
Saving it for the end. Most questions belong here. Write them down as they come, then go through the list when the inspector is on the ground. Ten minutes at the truck answers more than ten interruptions.
One practical note if you are tempted to phone them while they are still on the roof: on an iPhone, taking a call can suspend the stream. Not the inspection, not the recording of it — but your picture may stop until they are back in the browser. Better to wait.
The questions that are worth the trouble
These are the ones that change what happens next.
"Where is that on the house?" A close-up destroys all sense of place. Ask them to pull back and show you the same spot from far enough away that you can tell which side of the building it is on. Any inspector will do this and most will do it unprompted once asked once.
"How big is that?" Phone screens flatten scale completely. A crack you think is a foot long may be three inches. Ask them to put a hand, a pen, or a tape next to it. This is the single most useful question on the list.
"Is that normal for the age of this roof?" The most common misread is a homeowner seeing ordinary wear and hearing catastrophe. Ask directly. A good answer sounds like "that is about what I would expect at eighteen years" or "no, that is early," and both are useful.
"Is that active or old?" For staining, rot, and anything water-related. The difference between something that is leaking now and something that leaked once and dried is most of the decision.
"What would you do if it were yours?" Slightly unfair, and it works. It gets you past the hedging into an opinion.
"What did you not get to?" Every inspection has limits: a slope too steep to walk, an attic hatch painted shut, an area behind stored boxes. You want those said out loud rather than left as a gap you discover later. A good inspector volunteers them. Ask if they do not.
The questions that are not worth asking here
Price, in the middle of the walk. You will get a guess, the guess will be low or high, and it will anchor everything afterwards. Let them finish looking before they start quoting.
Anything about what other people will think of the record. An inspection documents the condition of a building on a particular day. What happens with that record afterwards is a separate conversation with separate people, and pulling the inspector into it while they are on a slope helps nobody.
"Can you go back?" They cannot, really. This is live, not a recording being played to you. Use the question button instead — that is exactly what it is for — and revisit the moment afterwards.
Save the list, then use it
Something I would tell anyone doing this for the first time: keep a notes app open beside the video and type as you go. Four words per item is enough. The urge is to just watch, and then the thirty minutes are gone and you remember two of the five things that bothered you.
If the question button is available, use both. Tap the button for anything visual, because the frame is worth more than your description of it, and write the word-shaped questions down.
There is a companion piece to this written for inspectors, homeowner questions during inspection, which is worth a look if you want to know what the person on the other end is bracing for.
What a question is actually buying you
Not reassurance. Understanding.
The reason live inspection is worth half an hour of your day is that it converts a document you have to trust into a thing you watched happen. Every question you ask while the inspector is still standing on the evidence widens that a little. Every one you swallow gets answered tomorrow, from memory, in a sentence.
If you did not manage to ask everything, all is not lost — the inspection is recorded, and getting your inspection records out covers how a copy actually reaches you. But the recording answers "what did they say." Only the live half answers "wait, what is that."
The mechanics of the viewer page, including the question button and what your inspector sees, are on the how it works page.
InspectStream records what an inspector observed. It is not a public adjusting service and does not prepare, negotiate, or advise on insurance claims.