Is it practical to generate onion addresses and attempt to connect to them via the tor client or is there a better approach? How can one get an estimate of the number of services available?
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It is absolutely impractical to shoot in random directions hoping to hit something. There are roughly 10^24 possible addresses, and roughly 10^4 actual live onions. (If you can do 100/sec, you will have 1 hit per 30 billion years on average.)
More viable methods are to run a crawler, or possibly to run a HSDir and log descriptors.
If you just want to find onions, see this question: How do I find onion sites?
