You likely have multiple problems going on. Incoming mail to an off network host like Conepuppy getting bounced is going to be an entirely different issue from outbound email thru a local SMTP server being lost.
Unfortunately any domain or IP that even remotely smells of porn or spam is going to be susceptible to being on some of these blacklists and thus losing mail. If your mail is hosted at any of the major adult hosts, there's a good chance they're on at least one list regardless of whether they run a tight ship or not. Small ISPs are also prone to getting listed because they often learn the hard way that they have to secure their network against spammers and end up getting listed.
The problems you're seeing are exactly why blacklisting doesn't work. They're impacting your ability to move email months later when the spammers have already long since moved on with no impact to them what so ever.
If you wanna have your own mail server, setting it up is only half the battle, you're in for some admin headaches. First and foremost you will want to secure it against spammers, make sure you're the only one who can send thru it. And before you even try, you need to confirm that your ISP will let you pass traffic outside their network on port 25 (smtp). I know in the case of Earthlink for instance, you cant pass port 25 to any IP other than their own SMTP servers. This is their way of trying to prevent spammers from setting up their own mail servers.
You must also have your reverse DNS and the identification of your SMTP server and headers neatly configured to be in full compliance. If your IP doesn't match the reverse lookup of the hostname you list for the SMTP server, it's not going to smell right to a lot of other mail servers out there and they'll bounce it or filter it as potential spam.
I'd be inclined to try to troubleshoot the problem with your local SMTP via your DSL provider. If Wig is using the same SMTP server and not having issues, the problem may be your domain name that you're putting on outbound email. I know from an email I sent you that Conepuppy is on one of the blacklists (i forget which), so if someone's mailer ignores your headers and does a lookup on your domain name and who holds the MX records for it, that may get that message blackholed even though the SMTP server it is coming from is perfectly clean.
Hate to say it, but it might be time to adopt a new domain as your primary email. And instead of parking it on Conepuppy, maybe do something like use Directnic's POP3 service.
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