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If you are going to be working with real wood grain baseboard or trim you will need to fill holes that you make with nails or brads while securing it to the wall. Nailing the trim to the wall not difficult and can be done by you or your handyman. Use the appropriate finishing nail or brad at the wall studs and countersink the nail head so it lies below the surface of the wood. A pneumatic nailer will do this for you, but you still have the hole to fill in.
The challenge is that wood putty doesn't accept stain like your wood trim does. Wood putty or filler will absorb more stain and turn darker than the surrounding wood. This won't look very nice on the finished piece as you will see exactly where the nail holes are.
If you can, hit the nails into the grain of the wood. The grain tends to accept stain more than the surrounding wood. If the grain lines up with the wall stud, hit it into the grain and fill it with putty. Sand or scrape the putty off so that the filled hole is flush with the surface, and then add stain and varnish. With an open grain like oak, you won't be able to tell where the nail holes are. You can also make your own putty using sawdust from the off cuts mixed with a little wood glue and stain.
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