The inserts were your weak spot. The shingles on the side of the home will be about 3/4" thick as a norm, not seeing exactly what you have and were you installed it on the siding, since some places the shingles are thinner.
To install the mount, it would be great to find the studs as Ed Beal recommends, but it is not possible in some applications. Depending on how long the inserts were you may be able to use the same placement as before, although I would not recommend it. BUT, if the inserts did not damage the subsiding under the shingles, THAT is where the strength is, under the shingles. The subsiding in that age of a house will be 3/4" to 7/8" thick solid wood, typically 1X6 or 1X8, but it can be anything wider too.
If you picked up in 12 ga. X 2" pan head or round head screws, (you may need to drill the holes in the mount a wee bit to get the screws to go in) and angled them into the original location, so they did not feed into the old location that the inserts were, they would find new material to tap into. By angling the screws I mean, in the upper left hole, angle the point to go left by about 10-15 degrees if the pole hole is not in the way. Same for the right side, but point the screw to the right. And the bottom hole, point the screws down about 10-15 degrees as well. To clarify, after the screws are in place, all the buried screw tips are farther apart, than the holes they went through. If you can shift the whole mount to the left or right out 3/4"- 1" then the screws can go straight in again since it will be beyond the damaged area from the original install and one screw will be between the original 2 holes at the top.
The best clue I have that the screws are holding, and yes, you can use a pilot hole for these screws, 3/16" is what I would recommend for either method, that when the screws go in and contact the mount, watch carefully tighten slowly and you will see the siding compress and sink the mount into the surface of the shingles. If it does not and starts spinning with out compression, the hold you need is lost. But if it deforms the metal, and sinks into the shingle, just a little, the hold is superior.