Everything's a risk until you get behind closed doors, which is why PPM is safest.
Never advance, either... even a regular, as she may very well take the money and run that one last time because maybe something drastic changed in her life -- or she decided to just cheat you. Been there, done that.
As for rides...
One of my now-regulars doesn't want a record of going to a restaurant or to a motel on her app, just in case her real daddy or the baby daddy looks at the app (or the bills, seeing extra-ordinary charges). She also sometimes doesn't really want to be seen hopping in my car, as I guess her family or neighbors might see me, but we do that in a pinch as I don't like paying for a ride when I can drive her.
For our first date, 2 years ago, I was able to Lyft her to the restaurant where we were meeting, and Lyft her home, though the app. Magically, at the time, I was able to figure it out and it worked without too much fuss.
Having the app pick up someone else has since been tricky for me, and I had to Google it just now to get a refresher.
For Lyft, where you see "me," click on the pull-down menu to "Change Rider/Add Rider" and go from there. Google "Lyft Rides for Others" for details.
For Uber, where it says "where to," click on your name above for the pull-down and select "Switch rider/Add a rider" and got from there. Google, "Uber Request a Ride for Someone Else" and you'll figure it out.
But I think you still have that risk where she could change the destination, so you'll want to message the driver.
Luckily that isn't a problem with me and my regular, but I'll have to save this info someplace safe in my brain as last time I was trying to get her to the No-Tell Motel, I wasted a bunch of our brief time together trying to get that to work, so finally got frustrated (and she caved) and I just picked her up.
To avoid any email or text privacy issues you or she may have (like if you're using a burner number), maybe just buy a physical gift card at the store, scratch off the numbers and take a picture or text it to her... if you trust her for $25 or whatever the cost would be. You can also send a Lyft or Uber gift through the app via text message or email (unless one of you has privacy issues).
Sometimes you gotta take a little gamble.