Unfortunately there isn't much more we can do on our end for this since it's Microsoft's decision not to accept mail from Tommy's IP. More often than not, this fixes itself over time as the IP's reputation improves. I tried sending an email from my own Tommy account to your Outlook account and it also bounced, so it is definitely the IP and not the sending email address.
We could offer you a dedicated IP for $20/year if you'd like in the meantime, which would separate your mail and websites from the rest of the users on Tommy. If you want to do this, let us know and we can set this up for you.
Or, you could move to Morty, which has a different (but still shared) IP. Morty has a recurring monthly fee, but it doesn't require you log in to keep it active, doesn't have a load restriction (you pay more if the load goes up, though since your account uses basically no load you'd just pay the base $1/month), and is quite a bit faster than Tommy too. If you want to do that, you can do it yourself: https://heliohost.org/dashboard/move/ (I've sent you a test email to confirm this option would work so you don't waste money if it's also blocked...)