Thanks for the response, I was worried the epic length post might not get an answer, forums in general you need to keep it short to get a lot of feedback (I actually edited it down a lot)

If using the pally to boost, he/she should not be on a linked account. Otherwise, you get no triple bonus and then you’d cry.
Thought so. So whatever number of accounts I want to end up getting gift levels with I'll need 1 more account than that if I want to try and boost with the pally, either by making all new accounts linked while keeping the main separate or by linking all but one of the new accounts to my main in chain fashion and then having a separate new account to transfer to. The question is is the increase in speed caused by having an unlinked pally boosting 2-4 linked lowbies worth the expense for my situation?

I’m giving myself 60 days to get as many characters leveled as possible. Then I’ll be transferring my other mains from old accounts to the three new ones and cancelling the old accounts. For the next two months, I’ll have 10 accounts active. I will whittle that down to 5 in 2 months. Give yourself a time limit to get things done so you don’t get carried away with the recurring monthlies.
See that's what frightens me, going for 2 and then up to 5 accounts doesn't seem that insane, but going to 10 (or as I saw one dedicated individual while browsing, 27 or so) accounts, that adds up to real money. Small difference between 15 bucks a month and 30 or even 45, but 60 or 75 is likely to cross a threshold, know what I mean? And that's based on how many copies my main comp can handle right now.

The gifted levels are not locked into a particular toon. You can gift the levels to any toon on the veteran account providing they are of lower level then the gifter.

I’m not sure I follow the 2nd part of the question.
I wasn't being clear I guess. My thought was say you have Main A linked to new B. B gains 30 levels on a toon, 1-30. B also has a 60 on the account via transfer. The gift levels generated by the 30 can't be "bestowed" by the 60. So a 45 on account A couldn't get those free levels generated by the 30 via the 60. As I thought about it it was a ridiculous question, as it would be so open to abuse it wouldn't be funny. So gifts can only be given by the toon that earned them, but any toon on the linked account can receive them, level permitting.

The big concern I have is being able to level fast enough while I can be playing to not waste the 90 day period. I've seen that some guys are making 5 toons into the 40s in like 9 or 12 hours or some ridiculous span. I'd love to churn out some power leveling and I know that the triple is a big help, but how much does skill, knowledge, and having the raw time to power like that effect it? Put another way, how fast can Joe Peon MultiBox Powerleveler (me) reasonably perform compared to the stud guys we have running around these and the EJ forums?

I guess if I did end up squandering the 90 day period I could just make a new trial, activate and transfer to it and cancel the old.

Upgrades I'm thinking 50 bucks to double my memory to 4GB with matching sticks may be worthwhile. My vid card is decent, my processor is dual core, so they at least should be kinda ok.

I do have multiple hard drives and plenty of space, I see varying opinions on multiple wow folders and putting the separate copies on different drives. Is this reasonable or balderdash?

Maybe I start small, get a second account and start powering around, learn the ropes a little bit, then see if I want to and can manage whole hog. Though that potentially gives varying 90 day end dates. The image of "shammy AE by 5 synchronized chain lightnings" does inspire a small evil giggle.

If you see the shammy in the threaded tuxedo pants with a spelldam mining pick running around Silver Hand's Bloodmyst Isle with a priest or lock in tow, that might be me.