Public Class Form1
    Dim mcheck(0) As CheckBox
    Private Sub CargarPropiedades()
        'Obtenemos la Lista de Enteros de los índices Checkados
        Dim ListaCheckados As Int32() = My.Settings.Valores
        For i As Int32 = 0 To mcheck.Length - 1 'Recorro los CheckBoxes
            For Each indiceCheckado As Int32 In ListaCheckados 'Por cada indice de CheckBoxes checkados
                'Como se los indices de los CheckBoxes checkados, accedo a éstos mediante el Array de los CheckBoxes
                'Ej -> indiceCheckado : 3 (CheckBox3) ;
                'Por lo tanto indiceCheckado - 1 = 2, mCheck(0) = check1, ... m(2) = CheckBox3
                'Es decir el índice N - 1 siempre corresponderá a CheckBoxN
                mcheck(indiceCheckado - 1).Checked = True
            Next
        Next
    End Sub
 
    Private Sub Form1_FormClosing(sender As Object, e As System.Windows.Forms.FormClosingEventArgs) Handles Me.FormClosing
        Dim mCheckados(0) As Int32 'matriz que guardará los indices de los CheckBoxes checkados
        Dim Cuantos As Int32 = 0 'cuantos CheckBoxes estan checkados
        For i As Int32 = 0 To mcheck.Length - 1 'Recorro los CheckBoxes en busca de Checkados
            If mcheck(i).Checked = True Then
                Cuantos += 1
                'Sumamos un indice por CheckBox checkado
                Array.Resize(mCheckados, Cuantos)
                mCheckados(Cuantos - 1) = i + 1 'metemos en el indice del Array el elemento Checkado (RECUERDA SE EMPIEZA DESDE 0)
                'Por eso lo de Cuantos - 1 (Si tienes 7 Checkados ira desde 0 hasta 6 ...)
            End If
        Next
        My.Settings.Valores = mCheckados 'Actualizamos la propiedades Int32()
        My.Settings.Save()
    End Sub
    Private Sub Form1_Load(sender As System.Object, e As System.EventArgs) Handles MyBase.Load
 
        For i As Int32 = 0 To 20
            Array.Resize(mcheck, i + 1)
            mcheck(i) = New CheckBox
            With mcheck(i)
                .Name = "CheckBox" & i + 1
                .Text = mcheck(i).Name
                .Location = New Point(40, i * 40)
            End With
            Me.Controls.Add(mcheck(i))
        Next
        CargarPropiedades()
    End Sub
End Class
 

    Dim mCheck(0) As CheckBox
 
    Private Sub UpdateArray()
        Array.Clear(mCheck, 0, mCheck.Length)
        Array.Resize(mCheck, 0)
    End Sub
 

Imports System.Windows.Forms
Imports System.IO
Imports System.Text.RegularExpressions
 
Public Class Form1
    Dim filesystem As Object, ThisDir As Object
    Dim mcheck(0) As CheckBox
    Dim winampargs As String

#Region "Propertys"
    Public Property userSelectedPlayerFilePath() As String
        Get
            Return playertextbox.Text
        End Get
        Set(value As String)
            playertextbox.Text = value
        End Set
    End Property
 
    Public Property userSelectedFolderPath() As String
        Get
            Return foldertextbox.Text
        End Get
        Set(value As String)
            foldertextbox.Text = value
        End Set
    End Property
#End Region

#Region "Load / Close"
 
    Private Sub Form1_Load(sender As System.Object, e As System.EventArgs) Handles MyBase.Load
        playertextbox.Text = My.Settings.playerpath
        foldertextbox.Text = My.Settings.folderpath
        updatecheckboxes()
    End Sub
 
    Private Sub Form1_FormClosing(sender As Object, e As System.Windows.Forms.FormClosingEventArgs) Handles Me.FormClosing
        Dim mCheckados(0) As Int32
        Dim Cuantos As Int32 = 0
        For i As Int32 = 0 To mcheck.Length - 1
            If mcheck(i).Checked = True Then
                Cuantos += 1
                Array.Resize(mCheckados, Cuantos)
                mCheckados(Cuantos - 1) = i + 1
            End If
        Next
        My.Settings.Valores = mCheckados
        My.Settings.Save()
    End Sub
 
#End Region

#Region "Save & Get settings"
 
    Public Sub GenerarPropiedades()
        Dim CheckedN As String = Nothing
        For i As Int32 = 0 To mcheck.Length - 1
            If mcheck(i).Checked = True Then
                CheckedN &= i + 1
            End If
        Next
        My.Settings.Save()
    End Sub
 
    Private Sub CargarPropiedades()
        'Obtenemos la Lista de Enteros de los índices Checkados
        Dim ListaCheckados As Int32() = My.Settings.Valores
        For i As Int32 = 0 To mcheck.Length - 1
            For Each indiceCheckado As Int32 In ListaCheckados
                mcheck(indiceCheckado - 1).Checked = True
            Next
        Next
    End Sub
 
#End Region

#Region "Draw checkboxes..."
 
    Public Sub updatecheckboxes()
        ' delete the old checkboxes
        Panel1.Controls.Clear()
        ' create the new checkboxes
        Dim filesystem = CreateObject("Scripting.FileSystemObject")
        Dim ThisDir = filesystem.GetFolder(My.Settings.folderpath)
        Dim i As Int32 = 0
        For Each folder In ThisDir.Subfolders
            Array.Resize(mcheck, i + 1)
            mcheck(i) = New CheckBox
            With mcheck(i)
                .AutoSize = True
                .Location = New Point(10, i * 20)
                .Name = "CheckBox" & i + 1
                .Text = folder.Name
            End With
            Me.Panel1.Controls.Add(mcheck(i))
            AddHandler mcheck(i).CheckedChanged, AddressOf LlamadaCheckBox
            i += 1
        Next
        CargarPropiedades()
    End Sub
 
    ' función que se ejecuta cuando cualquier checkbox es clickado
    Public Sub LlamadaCheckBox(ByVal sender As Object, ByVal e As System.EventArgs)
        Dim filesystem = CreateObject("Scripting.FileSystemObject")
        Dim ThisDir = filesystem.GetFolder(My.Settings.folderpath)
        Dim CheckboxN As CheckBox = CType(sender, CheckBox)
        If CheckboxN.Checked = True Then
            winampargs = winampargs & " " & ControlChars.Quote & Path.Combine(ThisDir.Path, CheckboxN.Text.ToString()) & ControlChars.Quote
        Else
            winampargs = Replace(winampargs, ControlChars.Quote & Path.Combine(ThisDir.Path, CheckboxN.Text.ToString()) & ControlChars.Quote, "")
        End If
    End Sub
 
#End Region

#Region "buttons"
 
    ' Folder button
    Public Sub C1Button3_Click(sender As Object, e As EventArgs) Handles folderbutton.Click
        Dim folderselected As New System.Windows.Forms.FolderBrowserDialog
        Dim Resultado As DialogResult
        folderselected.RootFolder = Environment.SpecialFolder.Desktop
        Resultado = folderselected.ShowDialog
        If Resultado.ToString() = "OK" Then
            userSelectedFolderPath = folderselected.SelectedPath
            My.Settings.folderpath = folderselected.SelectedPath
            My.Settings.Save()
            Dim mcheck(0) As CheckBox
            updatecheckboxes()
        End If
    End Sub
 
    ' Player button
    Public Sub C1Button1_Click(sender As Object, e As EventArgs) Handles playerbutton.Click
        Dim playerselected As New OpenFileDialog()
        playerselected.InitialDirectory = Environ("programfiles")
        playerselected.Title = "Select your favorite music player"
        playerselected.Filter = "Music players|mpc.exe;mpc-hc.exe;mpc-hc64.exe;umplayer.exe;vlc.exe;winamp.exe;wmp.exe"
        PlayerDialog.FilterIndex = 1
        Dim selection As System.Windows.Forms.DialogResult = playerselected.ShowDialog()
        If selection = DialogResult.OK Then
            userSelectedPlayerFilePath = playerselected.FileName
            My.Settings.playerpath = playerselected.FileName
            My.Settings.Save()
        End If
    End Sub
 
    ' Play button
    Public Sub C1Button2_Click(sender As Object, e As EventArgs) Handles C1Button2.Click
        Process.Start(userSelectedPlayerFilePath, winampargs)
    End Sub
 
#End Region

End Class

• Seleccionas un directorio
• Listas todos los subdirectorios
• Creas un checkbox por cada subdirectorio
• ¿Para que son las settings?