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Oil is the most important fluid in your motorcycle. I check before every ride. I have almost 600 miles on my new bike (owned for 11 days so far) and I have not had to add a drop of oil yet. No leaks, no smoke. Should have no reason to lose any oil. Check it every time and you can see any trends that may be developing. Enjoy.
Different models have different procedures. According to the manual for my Fat Boy, the bike should be "upright and level" for checking the oil cold and "upright on level ground" for a hot check. I've got a block of wood in the garage that fits nicely under the jiffy stand to make 'er level for cold checking.
But it's my understanding from some posts here on the forum that other H-D models are checked while on the jiffy stand.