I agree with basically everything posted above - mainly the route TOTALLYRC listed. Get parts that will cross over as much as you can and get what you need for the X1 and don't splurge on a higher level than is really realistic for the X1 that won't be able to transfer over to the IH. The biggest ? is if you want to go stepper or servo. If you go servo you may be able to move drives over but I am not sure - I don't have a lot of info on servo setups that are true servo systems. If you're going steppers than the 203V and a linear powersupply (homebuilt preferably) are a great basis for both machines. Doing the linear supply if you do a little research on what the X1 requires and what the IH will need later, you can choose a voltage that is scalable and simply buy another transformer later and double the voltage (ie - run a 40V 15 to 20A system on the X1 and then when you are ready for the IH add another transformer and capacitor [size the caps for the final target voltage] and you're ready to go - you might also be able to choose a toroid that has enough of a current rating to run the transformer secondaries in parallel on the X1 and when you move to the IH run the transformer in series - that route would save buying another transformer later, but require a really high VA rating to provide the increased amperage you'll need later for the IH - remember current is like the tank of gas in the car you can never really have too much, voltage is more like the octane rating). Other than the drive system you should be able to transfer over all the other electronics & software over since they don't care what they are hooked up to, it's more whether you want a higher quality limit or home switch for example that can fit on the IH but wouldn't fit reasonably on an X1. $2000 is a large budget for the CNC system in reality, especially if you design your own mounts and ballscrew setup instead of buying a kit - I forget what the tally for my X3 was but I don't think everything (including mill) was over 3k (it's posted in a thread by teyber somewhere here) and you'll have shorter screws, less material for the mounts, etc. I think you've got a good start. My advice would be plan and research before clicking the ORDER button

Having the whole system laid out and planned will increase your budget in effect by minimizing the amount of "Oh fudge!"s you run into

I bought my mill and then spent several weeks planning everything out and then designing and making the conversion parts and wiring everything up. The only backtrack was when I scored a free industrial grade enclosure for my controller and went back and redesigned the layout of the control box - well worth the effort I might add.
I agree that you shouldn't expect a great return on used items later with all the options out there and the presumed ease of a store bought CNC setup, unless you go the Hoss route and turn it into a real freak and can target it's uniqueness. Either go dirt cheap on the X1 conversion and save for later or buy now with research allowing you to step up later.
Good luck and keep posting your plans/ideas - the threads with the most information and plans get more attention it seems. People are always looking for a starting point for their work (as are you

) so they tend to get a lot of attention. Like the first response said - you already did a lot so you seem to have a good head on your shoulders and aren't asking the "what steppers do I buy" or "tell me exactly what I need" so you'll get great reception.
Several people have expressed appreciation for the information I shared about my X3 conversion so have a look at my website for any inspiration - there are pics, plans and some explanations and write ups there.
Greg