I had picked up an iron only once (to make an extension cable) before attempting my crack and had no issues. Just make sure you have some decent leaded rosin core solder and then take a few minutes to watch a youtube video or two on basic soldering. You will be good to go. Point to point is really easy. Before attempting the speedball, watch another video on through hole soldering.
If you like OTL amps, the crack really is damn good with hd800's, notwithstanding its modest price (assuming you find a tube complement that fits your preferences). There's a reason innerfidelity, headphonia, and guttenberg all recommend it as a great budget pairing with hd800's and that Tyll added it to his wall of fame. The crack isn't the last word in detail but is still quite a bit more detailed, dynamic and punchy than many other OTL's (i.e. Woos). As has been noted a time or two in the past, since Woo and most other OTL's don't load their tubes with constant current, the crack with speedball is a more sophisticated circuit. Having the space in the enclosure to throw in a pair of fat film output caps with low ESR and dissipation factor is the icing on the cake. (Fancy/slim aluminum cases have their appeal, but most aren't designed to accommodate caps of this size, and the output caps in OTL's are the final component in the signal path and definitely impact the sound.)
Crack isn't quite in the same league with the big boys (e.g. mainline, zana, etc.), but to my ears, it betters many higher price commercial options that are frequently recommended for high impedance phones.