Depends on the platform (desktop vs. mobile)... for desktop, I like Electrum. For Android stuff, probably Mycelium.
You could theoretically also just set up a wallet at blockchain.info and use that, without the need for extra software.
Read the sidebars of /r/DarknetMarketsNoobs and/or /r/BitcoinBeginners.
And the other guy is right, tumbling is pointless for random buyers. Just send coins from the source, to a private intermediate wallet (just use Electrum on your normal OS... forget TAILS, it's not for newbies and it's overkill), and then onto the market.
Tor Browser 5.5a4-hardened release available
The hardened series is built on top of the regular alpha series: it contains all the changes of the latter and further hardening, mainly against exploitation of memory corruption bugs. To this end Tor and Firefox are compiled with Address Sanitizer enabled (Tor even ships with another checker, the Undefined Behavior Sanitizer).
you should at least try tails, you don't have to know linux to use it. it warns you if your traffic isn't traversing tor -- it has a tor browser, a pgp tool, and electrum for a bitcoin wallet.
you'd typically use it on a usb stick and could more easily trash it -- cause it won't store anything on your computer. if you decide to use a "persistent" volume (a storage area on the USB stick to store some data) it will be encrypted. and if you use a persistent volume, it's also got a password manager to store your credentials for your unique identity.
be patient with it. give it an afternoon and go through the steps of setting yourself up, and then run through the process again after you have it down for all your steps. it's worth your while.
Yes, either of those two.
Electrum is free software, Helix is a service that costs 2.5% of the total transaction.
The whole point of a middle wallet or a tumbler is deniability.
hi i ordeda gram and finalized early. it was sent i you told me sop i escrowed 2 more igot a thing bout n ucouldnt so many people wanting eso i felt like a dick afterscrow all i needed was 2 grams the 3third was a present to one of the orange sunshine people my address isnt hot i get packages just not yours can i at least get the one i paid for please . https://privnote.com/v3XE7fwc#VmXuumyTF mistakes get made thats my address so i can get what i paid for instead of nothing iwhich made me poorer