Solution 1:

Potentially, but then no more than anyone with a regular domain name.

Spam filters look at the contents of e-mails to determine whether they might be spam or not and if you trust a sender you add their e-mail (either the specific address or the entire domain) to your whitelist.

Now, while your domain and address is random, it should be treated no differently to "normal" ones.

Solution 2:

I actually do exactly that on my Exchange Server: I create different e-mail addresses for every business I do business with, and associate them all with my account. I have Dell@, Symantec@, etc. If one starts getting SPAM, I can delete it, but I also know who is not careful with my e-mail address.

You will potentially run into problems, but not because of the domain name. How do you plan on sending the mail? The main issue that I can see facing you is the PTR record: Many domains, and most of the large ones, will drop your mail as SPAM if you do not have a PTR DNS record.

If you do not have a business class Internet connection with a static IP, you will not be able to get this (you have to ask your ISP to do it too), but all is not lost. You can pay for a relay service (smarthost), and relay all your mail through them, and they certainly have the requisite PTR record.

Solution 3:

I do the same thing in gmail: I use [email protected] when signing up for stuff.

Anything after the + is ignored by gmail - it will all still go to [email protected].

Solution 4:

In addition to what Chris said it also depends on the IP of your host. I deal with customers who get go daddy domains and domains hosted in eastern Europe only to find out the IP is on 20+ blacklists. Of course you can petition the list to get off. But be careful some unscrupulous providers have their entire blocks black listed and some of the black lists will refuse to remove an IP originating from said block.

It's tough to tell what IP you will receive until you sign up, particularly godaddy has 100's of blocks that they may be pulling from. http://www.mxtoolbox.com/ is a great resource for checking your blacklist status. Your best bet is to go with a reputable provider, hosting your relay from rack space or Amazon is great option since they can and will (I have personally seen it) change your IP if you are on a blacklist (unwarranted obviously).