Thank you for the responses. My annual spend isn't crazy, unfortunately. Its basically rental property I've bought to provide some sort of eventual retirement in 30 years (no pension for me.. just a lot of job volatility).

I've actually thought of spending the money for an LLC only to be able to get all the cards all over again! But commingling personal/business expense for LLC is bad bad bad. So these cards will just be sole proprietorships...

I am thinking that my annual spend will be ~$5-8K:
Insurance: $3.5K
Contractors/Maintenance: $2K
Transportation: $0.5-1K
Other: $1.5K

A few big expenses (> $20K each) will have to be paid with cash/check unfortunately.
And for 2013, I've unfortunately needed to make 2/3 of my insurance payments already (and couldn't put on my AMEX SPG).

the more I think about it, the strategy seems like it should be (i) one no-fee card just to have on any recurring payment streams (utilities). And then each year put all my spend on a single card for the bonus -- and swap the card each year (avoid annual fee).

Most bonuses are < $5K spend right. So i save all my insurance payments for same period, also around tax prep time.. should give me $4K spending at once in a April timeframe with plenty of time to spend whatever other minimums I need...