Well, after talking to various different people and a lot of hours reading different websites (offical and "fan") on different classes and a good bit of talking with myself and drinking...I'm as of this very minute leaning toward SM.
I'm going to go ahead and say my plan, and let whoever pick it appart if they care to

or say its a good plan, whichever.
Spec Miata
Sell s14
buy xx-93 1.6L miata
daily drive said miata
put a BAR in miata
do HPDE's with nasa untill both I and they feel I no longer suck
While doing HPDE's be modding the car and building for SM (OR pro7 depending on whether I decide i want to go with nasa or scca)
finally add the rest of the cage, no longer street safe (right? or is a well padded cage safe w/out helmet on street??)
At this point I get to figure out what to do as far as towing and what to daily drive etc...should be 2004 by this step. Another year of talking to people and driving should give me a more clear idea of where I want to go with this.
Why I favor this plan over others:
It allows me time to change my mind a hundred times while still having fun and learning with a car that has a future as a race car (very important to me opposed to having fun with a car that has no future...aka s14).
Buying a prebuilt car would mean I have to figure out all the details and things of towing that I just don't think I can do yet.
Basically...I think I was getting ahead of myself in the other plans.
I've never been a mechanic, i really suck at it actually...so a Spec class is probably the best way to go. If i lose I want it to be because I can't drive as well as someone else, not cauz of money or mechanical ability...tho I realize money and mech ability will be a factory in any racing, just much less in spec racing opposted to IT, HC or other more open classes.
If I run out of money for whatever reason, I have a fun street legal car that I can do the ocational track day in...hopefully it won't come to that.
So, what do you think?