populate "skip" labels in userform with the correct answer

Hi guys,
maybe somebody can help me, i need to populate "skip" labels in userform with the correct answer.
After i enter number in the textbox and press "Lookup" button in the userform it will populate labels (starting from "lbl1 to lbl32") with the data.
Basically what i need is when i type in something in the textbox i would like to activate skip label and then the skip label action would be to count how many bookings were made of that order number in that row and:
If that order was booked less than 10 times say "NO" in skip label
If that order was booked from 10 to 14 times say "YES" in skip label
If that order was booked 15 times say "NO" in skip label
If that order was booked 16-19 times say "YES" in skip label
If that order was booked 20 times say "NO" in skip label
If that order was booked 21-24 times say "YES" in skip label
If that order was booked 25 times say "NO" in skip label
Booking data is in the “Update” sheet

I just can’t figure it out how to do this, i will be very grateful if somebody can help me, I'm so stuck.
The file is attached for the reference.
Thanks in advance

You're just going to use a search (in vbe search box type range find) in the column for the skip value.

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to activate skip label and then the skip label action would be to count how many bookings were made of that order number in that row

I guess I don't understand this. Can you walk through a specific record and show what you expect.

Sorry Tinbendr,

I attached same file with the screenshots so it should be more clear for you what i'm trying to achieve.

I really appreciate your help,

Thank You very much

See if we're close.

I used the textbox change event instead of the Update button, so the change is immediate.

OK, I see the problem.

You have labels numbered left to right. I assumed top to bottom.

Try this version.

Hi yes it works thanks for your time maybe you explain me how it works and what you did?

Thanks

Since there are eight textboxes, I decided to write a subroutine in Module1 to handle the repetitive tasks. I pass the Order number and the label number to the subroutine. The Sub performs the search counting the number of order numbers. T,hen using the passed label number, updates the corresponding label with the Yes/No value using a Select Case.