UserForm Labels Drawn from Cell in Sheet

A userform's Initialize event is always called UserForm_Initialize, it's never called formname_Initialize and there's definitely no parameters passed to it.

So in the original code instead of this,

Private Sub BondAddUserForm_Initialize()

'***********************Open BondAddUserForm to Finalize Data for Bond Purchase***********************************************

Dim IssuerCap, BondNum As Variant, WS As Worksheet

Set WS = ActiveSheet

IssuerCap = WS.Range("O2")
BondNums = WS.Range("O7")

BondAddUserForm.Show

'Remind user of issuer and suggested purchase number

BondAddUserForm.Label1.Caption = "You are adding a " & IssuerCap & " bond to the ladder"
BondAddUserForm.Label2.Caption = "You can add up to " & BondNum & " bonds to the ladder"

End Sub

you should have this.

Private Sub UserForm_Initialize()

'***********************Open BondAddUserForm to Finalize Data for Bond Purchase***********************************************

Dim IssuerCap, BondNum As Variant, WS As Worksheet

    Set WS = ActiveSheet

    IssuerCap = WS.Range("O2")
    BondNums = WS.Range("O7")

    'Remind user of issuer and suggested purchase number

    Me.Label1.Caption = "You are adding a " & IssuerCap & " bond to the ladder"
    Me.Label2.Caption = "You can add up to " & BondNum & " bonds to the ladder"

End Sub