hmmm, I admire the enthusiasm and energy there! I don't often comment on build ideas, but many peopel have advised already perhaps a slightly less headlong rush into unknown territory, and I'm a bit inlcined to advise the same, you can still jump in the deep-end but perhaps start with copying a design on here that is well documented, suits materials and budget (and perhaps 2nd hand "finds" too), and will provide answers to many of your questions as you build and operate.
I'd start with finding a suitable boiler and heating method, a suitably sized column, packing and attachment methods/fittings, and then the simplest/quickest to assemble reflux method. Cooling management, although not that well regarded, is easy to set up, and although needs plenty of manual interaction, gives a great introduction to reflux control, wash composition, vapor temps etc, due to the amount of interaction it needs.
It's as simple as putting a cooling coil between the "top" of the column, and the output condensor - no slant plates, heads removers etc, required (although a reflux centering collar wouldn't go astray possibly), and if this is attached with slip-on fittings (sealed with teflon tape or flour paste), or screw fittings, it's not hard to add in liquid or vapor management, bokabobs, slant plates, reflux centering collars etc, later. It does require a needle valve for the cooling coil water, but this could certainly be used for LM later on. With a bit of juggling, it's possible to build a head that allows all three methods of reflux control to be tried.
It will provide the chance to start 'stillin as soon as possible (if that is desired), and also a test-bed for all the different ideas, the results of which could be posted. It's no fluke that after all these years there are some basic designs in LM, VM, CM that haven't changed much - although fine tuning is always happening, and anything new that works well, is, and would be, welcomed gladly!
On the monitoring and control front, for something really easy, simple and cheap, with huge amounts of support and info, one can't really go past "Stampplot" (a free serial graphing and control program, stampplot-"lite" is good to start with), and PIC microcontrollers, without a look, especially "Picaxes", an educational version with built-in serial bootloader (no programmer required), free downloadable "IDE" and "basic" compiler.
The chips are, well, as cheap as chips, and although diy is required, there are many pcbs, kits, and complete boards on the market to suit the level of assembly desired. They support a wide range of interesting devices (inc digital temp sensors eg) "natively" and allow ideas to be tried out very quickly without having to do a course in software engineering etc.
They can encourage poor programming and implementation practices, but do allow quick funcional prototyping before moving on to more industrial/professional methods/platforms (if desired), and very good for the hobbyist/amateur especially being low cost, popular, and well supported.
A wireless (or even wired to start with) thermometer feeding into a laptop/pc, would be a good first project for recording head temps etc, and still leave plenty of time to focus on the mechanics of a still build.
For a column, at least one remote temp probe and display is very useful to have, saves having to jump on a chair/ladder to read a thermometer at the head if it's a tall column.
At the end of the day, <edit: got a bit mixed up with another topic in "Fuel ethanol, but this comment still sort of applies too> , the feedstocks, sourcing, treatments, conversion and fermenting etc are also important, perhaps even more so, so I'd be gathering info on all fronts furiously!
Start simple with all aspects, get the idea, go from there - that will provide plenty of info and experience, quite quickly too. That's what I suggest...
