SMTP, hotmail rejecting email issue.

I am having a strange situation with hotmail rejecting emails from some of my domains.. I will provide as many details as possible.

I have 4 domains...  

I've been sending newsletters with authsmtp for years and never had any real issues.

Recently I was helping a friend send a newsletter from 2 of his domains (victorypoker.com and victorypoker.net) using authsmtp.com
Originally the .net domain would go to spam and the .com domain would not reach the account at all (completely rejected).

I added v=spf1 a mx include:authsmtp.com ~all to the .com's domain record.. I dont have access to the .net domain and the person added the record incorrectly.

Anyways.. after a month or so without do anything.. now .net gets completely rejected too..
I have another domain (playergps.com) that Ive always used authsmtp.com to send newsletters.. and now it also gets completely rejected.. so I tried another domain that use to work fine and hasnt sent any emails in over a year.. and it also gets rejected.

So I further continued to troubleshoot.. playergps.com sends email alerts (they are in HTML) with a different SMTP server automatically and regularly.. and those emails go to hotmails inbox no problem... I believe this SMTP server is local with its hosting... if that makes a difference.

I am using groupmail business edition 5.0 to send my emails.. it sends emails as HTML .. even if you just write something small like "test".. but there is a separate test function that I believe sends plain text emails.. when I do this with the playergps domain it goes to inbox.. does HTML make it more like to be considered spam?

I tried this with the other domains.. the victorypoker.net one still gets rejected.. victorypoker.com goes to spam.

So after this I tried outlook express 6.. playergps.com emails go to inbox.. victorypoker.com still goes to spam and victorypoker.net still gets rejected.

So Im curious how hotmails spam detection works.. it must give you some sort of score and things either increase or decrease the score.. and depending on the final score, it either goes to inbox, spam, or rejected?

does it make sense that HTML would make its score worse? or could it be groupmail? I just tested an email from playergps with outlook and HTML and it worked

Also I was curious if my IP had any impact on this, so i tried everything again when connected to a VPN and results were the same.

I ran a DNS report on victorypoker.com and everything came back clean..

Basically I need to get victorypoker.com to be able to send emails from my comp using a 3rd party SMTP.

I was thinking maybe it was an issue with authsmtp but it works fine with playergps domain in outlook express from my IP..


Sorry that this is a mess of random pieces of info.. I am just trying to remember all the details that could help solve the problem.