Finale 27.4, Windows 10, Sonar, (Cubase), Dorico Pro & Dorico iPad
This is not typical behavior. Is this the first time you have used this procedure since switching to Sierra?
Most folks who export PDF from Finale have been disappointed in the (flawed) PDF export included with the program and instead use a third-party PDF "printer" that installs as an option of your oper...
Have you accidentally switched layers?
Unless someone has turned off the handles, you should see two of them when you apply the articulation.
http://www.finalemusic.com/blog/compatibility-with-finale-notation-products-and-macos-sierra/
Now I see what you are after. ("Eso, si que es!" Did I get that right? It's been fifty years.) In Finale (not sure of PrintMusic) in Document Options > Beams there is a checkbox you would un-check....
I cannot send you a musx file via this forum, but I can give you another way of trying to enter your quintuplets. I do not use PrintMusic, so Finale may have some options you do not have. In Speedy...
You do not want a smartshape for this. (That is the glissando line you are using.) Use articulation #31 (metatool R for roll).
See if PrintMusic has the ability to turn off "check for extra notes" in the entry method (Simple or Speedy) that you are using. You can always turn it back on after you enter the quintuplets.
I'm not sure what you mean by "two by two" quarters in 4/4. Can you explain more fully or scan a drawing?