This should solve both problems. However, I have not tested this code because I don't have your file.
First, when you get an error, always provide the text of the error message.
A textbox contains...wait for it...text. You can't do arithmetic on a string so you have to convert it to a number first. That's what CDate does--converts a string to a date. Then you add 1. Then you may need to convert it back to a string for display in the textbox--maybe not, I don't remember if it will convert it for you automatically. Even if it is converted for you, it may not be the format you want. So a call to Format will display exactly the format you want; just use the string to specify what you want it to look like. Here I used m/d/yyyy.
Putting the Until condition at the end of the loop instead of the beginning will force the loop to execute at least once.
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