Regarding money, it may be a good idea to check out the thread about being paid as it's clear that the money situation changes drastically between regions. Some only get paid every three months, others every month, some start in November, others later. It might be a good idea to contact someone who was in your region (or the regions you've requested) to get an idea about the situation there.
I was wondering if any of the past teachers brought that amount ($2,000 USD) in cash, because you can get some hefty fees when transfering USD to EUROS especially when a bank is involved.
I kept it in my American account and made big ATM withdrawls.
While I was teaching in Germany I had a difficult time using my Capital One Visa card, because they only accepted European Credit Cards at most stores. Did any past teachers have this problem?
No, because the consejerĂa required we get Spanish bank accounts so that we could get paid by direct deposit. With the account, we were given debit cards. The other thing to take into mind is that they use cards here way less than we do back home.
When you open your Spanish account, make sure to do so once you've got, at least, your "resguardo" from you NIE (Spanish identity card). If you open it with your passport, you will get hit with hefty foreigner fees.
How did past teachers go about purchasing a cell phone in Spain? I wouldn't need anything fancy, probably the cheapest would do. Is it the same as Germany, prepaid phones? Do you need to be a resident of Spain (you had to be one when I taught in Costa Rica).
Prepaid. It's not necessary to be a resident (you'll legally be a resident with this program) but you must bring identification with you when buying the phone. Your passport or NIE will work.
One last question, for now, how difficult is it to get by with little Spanish skills. I took Intermediate Spanish in college, but that was a few years ago, and our standards of "intermediate" are much differen't than European standards - meaning that I probably only really have basic skills.
Depends on where you get placed. If you get placed up here in the not-so-touristy north, you'll find that out of school communication will be done entirely in Spanish. If you get into more typically touristy areas such as Alicante a lot more English is spoken. If you're willing to stick it out and to make mistakes with a sense of humor, you'll be fine!
Good luck!