Brian, good deal on the Kenwood. You can change out the connector for anything that will handle the current.
The way I mount roof top tri-pods is this.
1) find a desirable location and mount the tri-pod with nothing in it.
2) fasten it to the roof with the hardware included.
3) remove the single leg bolt and tip it over. The other two legs are hinged.
4) take your mast, and insert it into the tri-pod with no antenna mounted on it.
5) use a level to plumb the mast. There are adjusting bolts for doing this. I use 1-1/2 EMT for the mast on these easy jobs and they are strong enough.
6) lean the tri-pod with the mast over again and rest the mast on a saw hoarse (or what ever you have) on the roof.
7) while it's leaned over you a now have easy access for mounting the antenna and securing the coax down the mast.
8 ) raise the tri-pod, mast, antenna assembly up and secure the single bolt that keeps it in place.
9) check it again for plumb, and finish off the zip ties
10) Use Henry's 208 mastic around the mounting pads to weather protect.
I just looked at your out house J-Pole installation and you can lower the mast over and it looks like 10' of mast will hang over the eve. You can easily mount the antenna from a ladder. Or, you could mount everything up and slide it into the tri-pod but 10' of mast and 12' of antenna can be a little hard to handle by yourself so I do it as described above and it's a one man job.

Your done in about 45 minutes. The rest is running the coax to the operating station. When penetrating the side wall or however you penetrate the building, put a rain drip loop in the coax and seal up the penetrating hole with silicone.