Shannon:
I purchased the Historic Scotland Membership for one year for my wife and me. It didn't matter that we would only use it over a two week period (April 28-May 14, 2018) as it was a means to support a worthy "cause". It was good to have at Edinburgh Castle and Stirling Castle, we also used the card in the cafes. It was convenient to just walk in (not waiting in the long queues at both venues). If you're going to Inverness, membership also provides access to Ft. George. The website enter link description here (if you click on Free Entry to Historic Scotland Attractions) provides a map of all the venues covered by the membership. There are many more than one could visit during a 2 week stay in Scotland. As you're probably aware, Historic Scotland doesn't provide free access to all historic venues (including some well-known ones). Nonetheless, we thought it a good thing to do, and some benefits will continue throughout the year; we just received our first publication as a benefit of the membership. The membership "pass" was particularly nice to have in Edinburgh. We spent 3 full days and nights in the city , and returned to the Castle several times to see specific areas that had long lines or were very crowded on the first visit; when we subsequently returned we walked right in, no lines at all and we practically had the place to ourselves.
By the way, if you're going to Stirling (which I'd recommend), while you're in the area, make the short trip to Falkirk and visit the Falkirk Wheel (not historic, but an amazing piece of engineering), and make time to see the Kelpies (marvelous).
During our visit last spring, we made a similar journey as you're planning, except we Started in Edinburgh, then went to Inverness, Kyle of Lochalsh, Isle of Skye, Mallaig, Ft. William, Glen Coe, Oban and ended in Glasgow (with a day trip to Stirling). If you're interested in any specifics, send me a PM; I don't want to bore others reading the thread with the minutiae of our trip.