Yes, set the df and hope you get a ride. Chances are you will not get one all the way there, but will get something along the way. I was on colorado and i25 set my df to broomfield and got two pool rides to downtown and then another from downtown to pecos and 72nd, so it will take you towards where you want to go, sort of.
When I DF between FoCo and Denver, I'll usually turn it off in the more rural areas (south of Loveland or north of 144th). You almost never get a ride when in those areas while on I-25. I turn it back on with the DF as soon as I reach more built up areas.
So for the springs, I would say south of castle rock and north of monument hill.
I would just keep it on. What's it going to hurt? You can set it for shorter distances to if it doesn't let you do it the whole way you can set up for a Denver to Castle Rock and then Castle Rock 2 whatever towns between that Colorado Springs.
Keep in mind you'll get offered rides that will go sideways - if you're in Denver and set a DF for the Springs (dead south), you'll get rides offered on a 180 degree arc from due west around south to due east. You may even get rides that take you farther away than you wanted, due to having to backtrack to I25. It's rather ridiculous.
I live in Monument, you will have no problem setting your DF for the Springs from most of Denver. You will also have very little luck getting a ride from Denver anywhere South of Castle Rock (as others have said). However, on the way back to Denver, set your DF for the Denver airport and hang out in North Colorado Springs, you should be able to pick someone up going to DIA. Sunday afternoon/evening are best. Good luck.
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