Is this a valid AA award routing?

Trying to get from RDU to BCN in Biz using AA miles. I can find the following availability on individual segments, but AA.com won't show the entire thing if I search RDU-BCN, so I'm wondering if this is a valid routing:

• RDU-LGA saver economy on AA
• JFK-MAD saver business Iberia
• MAD-BCN saver business on Iberia

If I search AA.com for paid flights, I do see that RDU-LGA/JFK-MAD is one of their actual routings, so I'm assuming it'd be ok to add that initial RDU-LGA at the beginning of the JFK-MAD-BCN, right?

Also, I should be able to do an overnight stay in MAD as long as it is < 24hrs, correct?

So it'd be something like

• Day 1 RDU-LGA ~15:00-17:00
• Day 1 depart JFK ~21:00
• Day 2 arrive MAD ~10:00
• Day 3 depart MAD ~09:30 to continue to BCN as final destination

This would all price out @ 57.5k AA miles?

Additional bonus questions:

If I book myself using my AA account and my miles, and book my wife using her AA account and miles, then say she gets sick and is unable to fly... would we have to pay 2x$150 AA cancellation/redposit fees (as opposed to $150+$25=$175 if I booked both sets of tickets out of a single AA mileage account)?

Finally: if we are booked on 2 separate tix, one out of her AA account and one out of mine (to maximize the 10% discount since we both have AA credit cards), and she gets sick and can't fly -- assuming we both pay for taxes with CSR -- she gets a doctor's note advising her to not travel -- would CSR travel cancellation insurance cover both of our cancellation fees, or only hers?

Lots of questions, thanks for the thoughts/help!