Well this is pretty easy if you are any kind of computer smart, if you really need to ask about something just do it, here, not in a new post, here. Understood? Good.
Alright, first step on the long road to anonymity, never expect to be completely anonymous. The best you can hope for is flying under the freakishly large radar that is the NSA and other such governmental organizations we have probably never heard of.
Your best friends are Tor and a nice VPN if you can afford it, paid in cash or other non-traceable currency of course, I highly recommend TAILS as well for making orders, even for just browsing here and the markets if you really want to lock down. (I don't, but then again I don't particularly care) Don't know how to use TAILS? Google is your friend, I'm not here to guide you EVERY step of the way, do some research.
Never, for any reason, use e-mail addresses linked to your phone---no forget that, just DON'T use yahoo or gmail period. Here is a decent, but really well known I assume, temporary e-mail site. Now I encourage you to try and dig deeper and find something better and lesser known, but that's what I use myself currently and it seems to work most of the time.
So now we understand that we are never truly anonymous, know to use Tor and a VPN, and know to use a temp e-mail service, the next step, if you are going to start ordering soon is to get a PGP key, with at least 4000 some bits of entropy ideally, again, Google is your friend in this case so Google hard and if you still don't get it PM me or comment HERE.
Now you have a PGP key and you booted up TAILS to make your order, your palms are sweating as you open up TBB...you go to your favorite marketplace, but wait, you forgot your Bitcoins. Shit.
Alright so for completeness sake I'll let you in on how to get Bitcoins fairly anonymously as well, you pretty much have two main methods online (requiring bank information, not recommended unless you can find some service that will give you an anonymous bank account) or offline (best anonymity). Now either way you will want to tumble your coins, of course this is all in the sidebar but I highly recommend Helix as, supposedly, Helix blends "clean" coins whatever that should mean. Now that you have your tumbled coins, unless you tumbled a lot of coins for some reason deposit them DIRECTLY into your market wallet, if you deposit them back into your coinbase wallet you are a dumb shite and deserves what could possibly happen. If you tumbled a bunch of coins just deposit them in a secure offline wallet of course.
Now then, you have your tumbled coins in your market account and have the gleeful expression on your face that anyone gets when they are about to buy something they really really want. Again, make sure you are on TAILS, are using the TBB and hopefully a nice VPN or at the very least are in a public area in some dark corner to make your order. Place your order and, I assume (haven't gotten this far myself), wait for a response from the vendor. From there it's just about working out the details through PGP, I found a really cool onion service a while back where you could send a PGP message that would delete itself after it was read by someone. I can't for the life of me remember where it was, if anyone knows please do tell.
I hope this helps people and if I missed anything please let me know.
All of this is available in the side bar, written more professionally. Also, there was an article posted here that showed that a VPN plus Tor is actually worse than just Tor in terms of anonymity.