I would suggest that instead of checkboxes, you have the single line
descriptions added to a multi-select Listbox and then allow the user to
select the items that they wish to use.

Here is some code to get you started:

This routine loads a listbox with client details stored in a table in a
separate
document (which makes it easy to maintain with additions, deletions etc.),
that document being saved as Clients.Doc for the following code.

On the UserForm, have a list box (ListBox1) and a Command Button
(CommandButton1) and use the following code in the UserForm_Initialize() and
the CommandButton1_Click() routines

Private Sub UserForm_Initialize()
   Dim sourcedoc As Document, i As Integer, j As Integer, myitem As Range,
m As Long, n As Long
   ' Modify the path in the following line so that it matches where you
saved Clients.doc
   Application.ScreenUpdating = False
   ' Open the file containing the client details
   Set sourcedoc = Documents.Open(FileName:="c:\Company.doc")
   ' Get the number or clients = number of rows in the table of client
details less one
   i = sourcedoc.Tables(1).Rows.Count - 1
   ' Get the number of columns in the table of client details
   j = sourcedoc.Tables(1).Columns.Count
   ' Set the number of columns in the Listbox to match
   ' the number of columns in the table of client details
   ListBox1.ColumnCount = j
   ' Define an array to be loaded with the client data
   Dim MyArray() As Variant
   'Load client data into MyArray
   ReDim MyArray(i, j)
   For n = 0 To j - 1
       For m = 0 To i - 1
           Set myitem = sourcedoc.Tables(1).Cell(m + 2, n + 1).Range
           myitem.End = myitem.End - 1
           MyArray(m, n) = myitem.Text
       Next m
   Next n
  ' Load data into ListBox1
   ListBox1.List() = MyArray
   ' Close the file containing the client details
   sourcedoc.Close SaveChanges:=wdDoNotSaveChanges
End Sub

Private Sub CommandButton1_Click()
Dim i As Integer, Addressee As String
Addressee = ""
For i = 1 To ListBox1.ColumnCount
   ListBox1.BoundColumn = i
   Addressee = Addressee & ListBox1.Value & vbCr
Next i
ActiveDocument.Bookmarks("Addressee").Range.InsertAfter Addressee
UserForm2.Hide
End Sub

Private Sub CommandButton1_Click()
Dim i As Integer, j As Long, k As Long
Dim MyString As String

MyString = ""
j = 0
With ListBox1
   For i = 0 To .ListCount - 1
       '..and check whether each is selected
       If ListBox1.selected(i) Then
           j = j + 1
       End If
   Next i
   If j > 1 Then
       k = 0
       For i = 0 To .ListCount - 1
           If .selected(i) Then
               k = k + 1
               If k = 1 Then
                   MyString = MyString & .list(i, 1)
               ElseIf k < j Then
                   MyString = MyString & "; " & .list(i, 1)
               Else
                   MyString = MyString & " and " & .list(i, 1)
               End If
           End If
       Next i
   Else
       For i = 0 To .ListCount - 1
           If .selected(i) Then
               MyString = .list(i, 1)
           End If
       Next i
   End If
End With
MsgBox MyString
End Sub

The Initialize statement will populate the listbox with the data from the
table and then when a client is selected in from the list and the command
button is clicked, the information for that client will be inserted into a
bookmark in the document.  You may want to vary the manner in which it is
inserted to suit our exact requirements, but hopefully this will get you
started.

To make it easy for you, the code has been written so that it will deal with
any number of clients and any number of details about each client.  It
assumes that the first row of the table containing the client details is a
header row.

The method for determining which items are selected in the list box is give
in
the article "How to find out which Items are selected in a Multi-Select
ListBox" at:

http://www.word.mvps.org/FAQs/Userforms/GetMultiSelectValues.htm