I've been a longtime user of the National Geographic TOPO! series. One of the tools they offer is freehand route drawing: you just click on the 'pencil' and draw (with a mechanism to erase the track), and click to stop drawing. This makes it pretty easy to trace a route along a trail (to whatever level of detail you feel necessary), and is (IMHO) easier than the 'draw a track' mechanism in TF -- the latter results in more point-click-point-click repetition, particularly for trails which aren't straight lines.
Why would I do this? If I'm planning out a hike, it's nice to follow the trail and get a good idea of both the distance covered by the trail plus the elevation profile of the trail, instead of doing straight lines between the interesting waypoints.
(On thinking about it, another feature of TOPO! that is nice is that if you hit a screen edge while drawing, the map will automatically scroll some distance, so you never need to stop drawing; in TF I have to stop drawing, switch to the hand tool, and start drawing again.)
My first, and specific, suggestion is thus to allow for this free-hand style of drawing rather than the current segment at a time.
Now I will go off into dreamland...
The idea for "better route management" is something that's been growing for a while as I've played with various map programs. The general idea is that I've picked a place to go (and in my case, go backpacking) but I haven't narrowed down exactly what to do yet. I can leave from a given trailhead (TH) and do several routes (call them routes 1, 2, 3) and stop at one of several places for my campsite (call them sites A, B, C). Some parts of routes 1,2,3 are in common (same trailhead), some aren't.
With most programs, including TF, I need to draw out every option (route 1 is TH -> A -> TH, route 2 is TH -> A -> B -> TH, route 3 is TH -> A -> C -> A -> TH, for example), and either lay all the routes on top of each other -- which is hard to do -- or draw a route, save it, clear it, draw a new route, record the data, clear it, etc.
It Would Be Nice if I could add another level of indirection and draw segments, then connect segments together into routes (maybe aggregating routes into trips).
In terms of my example above:
I draw a 'segment' a that is TH -> A.
Route 1 (one day's hike) is just segment a, Trip 1 is Route 1 in both directions.
I draw a segment ab that is A-> B, and a segment b which is B -> TH.
I've now got a couple of options:
Route 2a combines segments a and ab (so it goes TH -> A -> B), and Route 2b combines segments ab and b (so it goes A -> B -> TH). (Basically, I'm trying to figure out where to camp one night.)
Trip 2A has Route 2a for the first day, and a route that's just segment b (hiking B to TH) on the second day.
Trip 2B has segment a (TH->A) for the first day, and Route 2b (A -> B -> TH) for the second day. Both of these Trips cover the same terrain but the Routes I travel are different.
This may sound complicated but it's basically a manual form of what a trip planning program like Streets and Trips or TopoUSA lets you do. What I'm hoping for is a way to think about a trip as a whole and on a per-day basis, including adjusting the route accordingly ("what if I go THIS way? what's the elevation profile if I stop HERE, rather than THERE?").
I can certainly understand if your response is "way too hard and not worth it," but I figured I had to try.