Newbie Stencil Project Fail.....Advice or suggestions please......

Submitted to Community Café

Hoping for possible tips and advice from the pros here please.

I’m using a new vinyl cutter to make stencils to achieve the nice crisp lettering that I admire seeing here.
Many of my projects are failing for one reason or the other, trying to isolate if it is the technique, paint or vinyl or a combination.

The failure always seems to be with removing the stencil.
On a prior project I learned that a cured? base coating seal layer of modgepodge can somehow resoften ( with adhesive application) and pull up. I won’t try that again.

Here I’m trying to make an outdoor -house number sign.
Used American Accents ultracover premium latex gloss black on a piece of previously painted then sanded wood. It was a gloss black base coat several coats painted weeks ago. Fully cured.

I placed the Oracal 631 stencil on top.
Sponged light coats of white latex and let it dry for several hours.
Tried to roll the stencil off and it pulled a substantial amount of the acrylic white paint off—- and also to my horror the top base coat -black glossy background coat of the ultra cover off precisely below the numbers. I’m guessing the parts of the white paint stuck with the stencils cut edges and rolled off with it.

Do you suppose it’s my technique of pulling off the stencil?
This project has been painted several times and it’s difficult to see the woodgrain determine which direction to pull.

Can gloss paint be used?

Wrong vinyl? Can the stencil adhesive be too strong for these types of projects?
Is it better to pull the stencil off while paint is wet?
Is more than one coat discouraged?

If you have any suggestions to any sucessful stencil sign painting procedure please let me know -to help my learning curve.
Either things not to do or things to do.

Unfortunately - I never see the fail reels in the YouTube or written in internet tutorials -to help with learning do and don't. 

So please leave your suggestions and stenciling tips here if you have any. Many thanks for your time and trouble to read this and offer any advice. May the kindness and good karma be returned to you.