Just set it to match ANY of the following conditions.

the "or" and "and" (match all or any) conditionals appear at the top of the dialog box when you add more than one selection criteria

Note as well that you can only do "and" or "or", not a combination. For example, there is no easy way to do the following:

(genre=ska OR genre=punk) AND rating is 5

This type of combo is definitely beyond the scope of smart playlists, but can be accomplished on the mac with a combination of smart playlists and applescript.

Thanks for all the help. Two questions, one related.

With the above parameters (i.e., play count and rating), it it possible to eliminate the songs I have rated 1 star, as well? If so, and it's an applescript, can someone point me or tell me the script to use (may need help on how to do it, as well).

Second question relates to a comment about shuffling my library in iTunes and then letting that play on my iPod. How does one do this?

After all this discussion you could accomplish what you laid out in your original parameters:

Match all the following conditions:
Last Played - is not in the last - 5 days
Play Count - is less than - 5
My rating - is in the range - 4 to 5

I'm mis-stating my question then. What I want to do is play all songs not played in the last 5 days, whose play count is less than 5 PLUS any songs with a 4 or 5 star rating AND not play any songs with a rating of 1 star at all (those are ones I keep but don't wish to hear until I listen to cull them out - I keep them because they are album tracks I don't wish to lose yet).

As to the shuffle question, I must be dense because I don't know how to shuffle iTunes, unless that means to turn on the shuffle button (does doing so apply shuffle to everything on iTunes as long as it's on?) What does your comment 'sorted by playcount' have to do with shuffling? So, if I get this, I turn on shuffle in iTunes, then select my iPod smartplaylist with the above parameters and turn off it's shuffle. I guess the shuffle on in iTunes freezes the shuffle order of the smartplaylist and then when it is played on the iPod, the shuffle order applies until I resynch with iTunes????

For shuffling, create a playlist. Then click the shuffle button. If you then click the top of the column all the way to the left of the columns (the one with the numbers). This will sort by play order.

When you sync this list, it will keep the order of your sort.