>Have you checked out the HELP on the FOR command? There seems to be some options available (beyond what was available in DOS) that could come in handy.
>
>Maybe something like this (haven't tested this)?
>

>@ECHO OFF
>DIR /B /OD LPT$VPN.* > C:\TMP\MYLIST.TXT
>SET LastF=
>FOR /F %%i IN (C:\TMP\MYLIST.TXT) DO SET LastF=%%i
>IF [%LastF%]==[] GOTO Quit
>FOR /F %%i IN (C:\TMP\MYLIST.TXT) DO IF NOT [%%i]==[%LastF%] DEL %%i
>SET LastF=
>:Quit
>DEL C:\TMP\MYLIST.TXT
>

The FOR /F was key, as you suggested. I reduced it to the following (8 commands in total, only 2 are really necessary):

@ECHO OFF

REM Set the wildcard string of the files to be deleted:
set FileWild="LPT$VPN.???"

REM Set the value below for the "n" MOST RECENT files to be NOT deleted (i.e. skipped):
REM set /?
REM http://www.microsoft.com/resources/documentation/windows/xp/all/proddocs/en-us/set.mspx?mfr=true
set /a NumSkip="2"

REM This command writes all files matching the wildcard string to FileList.txt
REM in REVERSE DATE ORDER, i.e. most recent at the top:
REM dir /?
dir %FileWild% /o-d /b >FileList.txt

REM This command parses the FileList.txt file line-by-line
REM for /?
REM http://www.microsoft.com/resources/documentation/windows/xp/all/proddocs/en-us/for.mspx?mfr=true
REM /F instructs the for command to parse
REM "skip=%NumSkip%" to skip the first NumSkip lines
REM (so those files won't be processed i.e. deleted):
for /F "skip=%NumSkip%" %%I in (filelist.txt) do erase %%I

REM Cleanup:
erase FileList.txt
set NumSkip=
set FileWild=