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What do you guys think of running 4 portfolios of this (one per quarter) each looking out a year or 6 months ahead on the expiration date.

In general, if you're following the suggested formula to any close degree, it's a pretty safe strategy.
The one main way it can fail is if some of the stocks you're long go down, but the broad index you're using for your hedge doesn't.
This risk is substantially reduced by diversification.
It's possible for six things to go down but not the index, but it's extremely unlikely for 30 things to go down but not the index.
So, for risk mitigation, the main thing to bear in mind is to have lots of positions, in many sectors, to the extent that your portfolio size allows is.
So staggered portfolios would make sense not just for the advantage of avoiding inopportune entry dates, but also because you'll likely have more names.

If you're willing to deviate from the suggested strategy somewhat, I would suggest the following:
Go a little non-mechanical with your dates.
In any given quarter, try to enter your longs on days which the omens might suggest the market is a bit lower than average,
and enter your hedges when the market seems to be toppy.
If you do it on multiple dates, I speculate that it's not so hard to beat a random number generator at that task.
You could determine those days mechanically...e.g., open long positions (short puts) only on a day that's the lowest in the prior 4 weeks.
Lowest for the market, or lowest for that stock.
And vice versa for the hedging short positions. (long puts).

After a few years I ended up entering positions quite regularly, when the thing I want to be long looked cheaper than usual.
And changed positions sizes accordingly, too...if it looked richly priced I entered fewer long positions (short puts) and vice versa.
It gradually became entirely non mechanical, but averaged over time still the same overall general strategy.
A broad portfolio of short puts, and some number of long index puts for disaster hedging and to give the confidence for a little leverage against the cash pile backing it all up.

Jim
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