We didn't do the love away plan, we went through our TA and booked the room when they ran a special for next year and then booked our air fare later. Hope this helps, next year will be our 4th year at CN.
I check out everywhich way but loose to book and then use the best method which combines price with other variables such as insurance offerings, frequent flyer miles etc. There is no right or wrong way to book. Just the one that makes the best sense to you.
Having said that I've been to CSA 5 times and never booked the same way twice. Used brick and mortar travel agent, airline website, internet website, Costco website and Couples website.
I used the Love away Plan for both our New Years and April 2013 trips and booked it differently both times. For me it depends on the time of year I'm booking. If it's a busy time, I start watching the price of the flights 10 month ahead. For the New Years trip I booked air first when I saw a good price and then booked the room as soon as the 2013 prices went up on the Couples website.
For the April trip I booked the rooms first back in May and got the resort credit. Now I'm watching for a good price to come up for the air.
BTW, we're from Canada and we can't get a direct flight if we booked the land and air through Couples so for us that's not an option.