Task: Straddling checkerboard
Java: import java.util.HashMap;
import java.util.Map;
import java.util.regex.*;

public class StraddlingCheckerboard {

    final static String[] keyvals = {"H:0", "O:1", "L:2", "M:4", "E:5", "S:6",
        "R:8", "T:9", "A:30", "B:31", "C:32", "D:33", "F:34", "G:35", "I:36",
        "J:37", "K:38", "N:39", "P:70", "Q:71", "U:72", "V:73", "W:74", "X:75",
        "Y:76", "Z:77", ".:78", "/:79", "0:790", "1:791", "2:792", "3:793",
        "4:794", "5:795", "6:796", "7:797", "8:798", "9:799"};

    final static Map<String, String> val2key = new HashMap<>();
    final static Map<String, String> key2val = new HashMap<>();

    public static void main(String[] args) {
        for (String keyval : keyvals) {
            String[] kv = keyval.split(":");
            val2key.put(kv[0], kv[1]);
            key2val.put(kv[1], kv[0]);
        }
        String enc = encode("One night-it was on the twentieth of March, "
                + "1888-I was returning");
        System.out.println(enc);
        System.out.println(decode(enc));
    }

    static String encode(String s) {
        StringBuilder sb = new StringBuilder();
        for (String c : s.toUpperCase().split("")) {
            c = val2key.get(c);
            if (c != null)
                sb.append(c);
        }
        return sb.toString();
    }

    static String decode(String s) {
        Matcher m = Pattern.compile("(79.|3.|7.|.)").matcher(s);
        StringBuilder sb = new StringBuilder();
        while (m.find()) {
            String v = key2val.get(m.group(1));
            if (v != null)
                sb.append(v);
        }
        return sb.toString();
    }
}

VB: 

Function encrypt(ByVal originalText, ByVal alphabet, blank1, blank2)
  Const notEscape = "0123456789ABCDEFGHIJKLMNOPQRSTUVWXYZ."
  Dim i, j, curChar, escChar, outText
  Dim cipher  
  Set cipher = CreateObject("Scripting.Dictionary")
  
  alphabet = UCase(alphabet) : j = 0
  For i = 1 To 28
    curChar = Mid(alphabet, i, 1)
    Select Case True
      Case i>= 1 And i<= 8
        If j = blank1 Or j = blank2 Then j = j + 1  
		cipher.Add curChar, CStr(j)
        j = j + 1
      Case i>= 9 And i<=18
		cipher.Add curChar, CStr(blank1) & CStr(i -  9)
      Case i>=19 And i<=28
		cipher.Add curChar, CStr(blank2) & CStr(i - 19)
    End Select 
    If InStr(notEscape, curChar) = 0 Then
      escChar = curChar
      
    End If
  Next 
  For i = 0 To 9: cipher.Add CStr(i), cipher(escChar) & CStr(i): Next 
  
  originalText = UCase(originalText)
  For i = 1 To Len(originalText)
    outText = outText & cipher(Mid(originalText, i, 1))
  Next 
  encrypt=outText
End Function 
 
Function decrypt(ByVal cipherText, ByVal alphabet, blank1, blank2)
  Const notEscape = "0123456789ABCDEFGHIJKLMNOPQRSTUVWXYZ."
  Dim i, j, curChar, escCipher, outText
  Dim cipher  
  Set cipher = CreateObject("Scripting.Dictionary")
  
  alphabet = UCase(alphabet) : j = 0
  For i = 1 To 28
    curChar = Mid(alphabet, i, 1)
    Select Case True
      Case i>= 1 And i<= 8
        If j = blank1 Or j = blank2 Then j = j + 1  
		cipher.Add CStr(j),curChar
        j = j + 1
      Case i>= 9 And i<=18
        cipher.Add CStr(blank1) & CStr(i -  9), curChar
      Case i>=19 And i<=28
        cipher.Add CStr(blank2) & CStr(i - 19), curChar
    End Select 
    If InStr(notEscape, curChar) = 0 Then
      
      arrayKeys=cipher.keys
      escCipher = arrayKeys(cipher.count-1)
      
    End If
  Next 
  For i = 0 To 9: cipher.Add escCipher & CStr(i), CStr(i): Next 
  
  i = 1
  Do While i <= Len(cipherText)
    curChar = Mid(cipherText, i, 1)
    If curChar = CStr(blank1) Or curChar = CStr(blank2) Then
      curChar = Mid(cipherText, i, 2)
      If curChar = escCipher Then curChar = Mid(cipherText, i, 3)
    End If 
    outText = outText & cipher(curChar)
    i = i + Len(curChar)
  Loop 
  decrypt=outText
End Function 
 
  message = "One night-it was on the twentieth of March, 1888-I was returning"
  cipher = "HOLMESRTABCDFGIJKNPQUVWXYZ./"
  
  
  
  
  Buffer=Buffer & "Original: " & message & vbCrlf 
  encoded = encrypt(message, cipher, 3, 7)
  Buffer=Buffer &  "encoded: " & encoded & vbCrlf
  decoded = decrypt(encoded, cipher, 3, 7)
  Buffer=Buffer &  "decoded: " & decoded & vbCrlf
  Wscript.Echo Buffer