I've done it a few times on older houses with wood lap siding that is similar to what's in the picture.
Hardie's biggest issue is that it's brittle. It needs a wood backing. OSB or plywood is the most common because it's the cheapest, fastest and easiest to install on new construction. Having thicker wood is a plus.
I've read that you should never double your vapor barrier with something between it. Most of that deals with insulation. In my opinion, if there is a vapor barrier under the wood already, it's not significant enough to not install house wrap over the wood siding.
I clean up the existing siding and smooth out any areas that might be sticking out. I want the Hardie to be flat against the wood. I go ever every board to make sure it's tight. A lot of them are installed with finish nails, and they like to work their way out. I remove loose nails and install screws.
I haven't checked the Hardie website lately, so it's something you should do before installing it. They have instructions on how to do it. I use a coil roofing gun with 1 3/4 inch nails that I put in every foot or so. I think Hardie want's them on every stud, but that's almost impossible to do, so I try to hit a stud where I can, but I'm not too worried if I just hit OSB.
The big issue is the nail head must not damage the Hardie. They want it snug, or even almost loose. Setting the depth on the nail gun means it's strong enough for a stud, but then it damages the Hardie if you only hit OSB. In your case, it will be a lot easier to set the depth on the nail gun since it's all solid wood.
Home Depot sells Hardie blades. They have a small one that's cheaper, and a 7 1/4 inch blade that's a lot more money. The big blade lasts forever, but it's impossible to cut straight with. I don't get it, but it's the biggest waste of money ever. I just buy the small blades now. I can do an entire house with a small bade if there isn't a lot of trim. I just use my 18volt Makita cordless saw to cut everything.
Smart Siding looks similar to Hardie when installed. It has a lot of good qualities, and it's a lot easier to install. I use a sealer primer on everything I cut before I install it. For my house, I use Hardie. For clients, I let them decide, or if I'm matching what's already on the house, then that's what I use. The finish look is always the most important for the client, and I'm comfortable with both products being good enough to last and make my clients happy.
