1) Assume that the iPod flash has 1,000,000 writes. (It should have at least this much.) There are 365 days in a year. For simplicity of math we'll round up to 400. If you shut down once a day, you write once a day. At 400 days a year (more than a normal year) you get: 2500 years. Now, assume you do it twice a day. 1250 years. 20 times a day? 125 years. Do you think your iPod will last this long?
2) Rockbox just doesn't *have* a sleep mode yet. The reason it doesn't put it into a light sleep mode is an entire lack of one being written yet.