Miles and $$ combo
 

This is my first post on this list. =)

I would like to use a combination of money and miles on CO to fly first class to Asia. Which would be better: buy coach and upgrade with miles, or get coach with miles and then spend $$ to upgrade? Or is this combo idea not smart at all? Thank you.

It depends what your budget is.

On CO today I booked flights to Hong Kong next week in Y. I could purchase an upgrade for around 4,000 each way or I could do 30K miles and $600 so I went with that option.

In Oct I'm flying to Hong Kong on United and was able to get a rare upgrade to First from Y for $999 each.

Wow, you only spent $600 to upgrade to first class? That's a good deal.

Plus 30K miles, a not insignificant sum.

And correction, an upgrade from coach on CO would be to business, not first (though the "BusinessFirst" terminology is quite confusing, I agree)

Booking a coach award ticket and then expecting to buy up with cash is a recipe for disappointment. Odds of that working out are very slim.

Depending on the fare you pay for the coach revenue ticket the co-pay can be significant in addition to the miles required. I generally find that upgrades are a bad deal these days most of the time.

I agree. I just called CO to inquire about this and they said it is not doable to get a coach ticket with miles and use $$ to upgrade to First. They said the reverse is possible but it would cost A LOT of points.