I think I see the problem, Berin. Try this instead, please.
1. Create an A to B route. By default, MyRoute displays the two points as hands, which are numbered: Point A (start) is number 1 and point B (end) is number 2.
2. You can shape this simple A to B route in one of two ways:
i. I guess you are using the ‘Place waypoint’ tool?
View attachment 284463
Using this method will add a point at the end of the route by default, in effect giving you a new end point B, numbered 3. As you say, you then have to re-order these manually. In essence, this method is only of any real use if you build a route in stages, starting from A then proceeding, road by road, until you reach your final destination.
Instead, try this second method. Here is an example, using my iPad.
ii. Click and hold (or give a sharp tap) on the black line of the route, near enough where you want to shape it. I find that there is a bit of a knack to this, or at least there is using my iPad. A dialogue box will pop-up, asking if you wish to rename this new point. Name it if you want to.
View attachment 284464
Click OK
A shaping point will be created at that point, It will be numbered 2. In other words it falls not at the end but between point 1 (start) and what is now point 3 (end)
View attachment 284465
Drag point 2 to the road you which to take. Again, you’ll see an option to re-name it if you want to. The route will then reshape.
View attachment 284466
If you then open up your list of waypoints, you’ll see it there, in its correct point 2, shown as a tear drop shaping point. No more manual re-ordering required. All sing, Alleluia!
View attachment 284467
You can then change the shapoing point into a hand via point, if you want to. Or just leave it as a shaping point.
View attachment 284469
Repeat as necessary, until the entire route is shaped to follow the roads you want it to follow.
Note:
1. Using 1.2 to transfer to your XT, should show every ’hand’ as a flag on the XT.
2. Each flag should show as a choice of possible destination(s), when you first fire up the route on your XT.
3. There is a bit of a knack to shaping any A to B route. I generally start roughly in the middle of the route to place my first shaped point. That being said, in reality, it’s no different to shaping an A to B route in BaseCamp.