My advice would be to go explore yourself first. It may depend on how convenient it is for you to go to Skye and if you're looking to just get the munros bagged, so to speak. If the latter then a Guide may be best. If you're happy to accept that you may not always come away with a summit in the bag, then go yourself. Apart from the walk ins, the level of fitness required would be about the same for climbing stairs all day
Couple of things worth mentioning, Skye is less about navigation in the true sense, map/compass etc, but more about familiarisation with the various routes, knowing what features (notable rock features and such like) to look for confirming you're on track etc. navigation comes in to get you to a point, up the particular glen and so on. Once on the ridge, this knowledge of such features plays a bigger part and in the mist it can be very confusing, the ability to follow a compass bearing (and there are places where the compass will not be true, GPS or similar probably more use), is rather immaterial, as you'll probably be able to go forward or back, either side being less of an option for obvious reasons. Noting wind direction also as an aid to the direction you're pointing, are you going up when you feel you should be going down, the usual route finding techniques. Lastly, once on the scrambly sections, don't make any move that you cannot reverse, and if it looks impossible, look around, there is probably another way, one that others have used, scratch marks from crampons, rock discoloured, bearing in mind that many folk over the years will also have nade the same mistakes, so don't take these signs as being the route
My first trips to Skye were infrequent, as I lived down south, so it would have been a one weekend a year trip, and not all those were to Skye. It was 30 years to reach 50 Munros. Clearly living up here helps and you could compress the Skye trips into a year. But like you the first time I read of the Cuillin it gave me goosebumps too. But over the years have had many trips, and many turning back, but none without learning a little more, becoming familiar with the walk ins and so on.
First time to do Alasdair via Sron na Ciche, (picked that route so I could look down on the Cioch
) we arrived at the 'Bad Step', just an awkward corner, form which a slip would certainly hurt (a sling can be useful to hold on as you take the step round onto the continuing ledge. But after that we could not see the way on, it wasn't obvious, a drop down to a col and then this huge impenetrable bulk in front, where do we go, we know the summit is up there !! Luckily a party of two came up from Coire Ghruinnda and proceeded to climb a small chimney which was the key, but difficult to see from our stance further back, once up that it was just a case of picking a route up. Down the Stone Shoot (I've never gone up it
).
Similarly, the walk up into An Dorus,, I seem to have a habit
of missing the slight deviation to An Dorus up near the top and ending up at the bottom of the Black Notch ( I now have a large boulder firmly engraved in my memory as the key to keep left and not follow the other path, although it might be worth a look, albeit wet, you pass the top of it on approach to Greadaidh), and the first trip to An Dorus we turned right climbed out to do Greadaidh, as Mhadaidh filled us with fear, when in fact it is relatively easy either by going through An Dorus by a few steps and turning back up, or easier still there is a faint path on the left where the An Dorus gap starts to close in. On the way up this way there are even areas of flat where folk no doubt bivvy when doing the whole ridge.
First time seeing the Inn Pinn, I declared 'I'm never getting up that', I even put a cursory tick in my Munro book, because I had touched it
But many years later a new found friend, went up it on his own, with a coil of rope for the abseil, he was up in 5 minutes. He took myself a few years later, longer than 5 minutes, but I had done it, if it wasn't for its position, it would be no worse than any other scrambles that you've already done. Its also the only one I wore a helmet for, although given my helmet had had its use caving for protection from falling stuff, I wasn't convinced to wear it even for the Inn Pinn, the drop being such that I failed to see the benefit of only having my head intact
Its all easier to get familiar if the weather plays ball, as I said it can be a confusing place in mist when up amongst the rock, boulders etc. But first time, doing some of the more straightforward ones, be sure to look across to others to pick out the features that you can read up on, it all adds to the knowledge for the future trips. Depending on who you are with, it can be useful to have a small length of rope, say 25 to 30 foot and a couple of slings/carabiners for some bits, folk with small legs and such like
I seem to have a few friends that are challenged in that area
So, basically I would go yourself, find all this out for yourself, its so much more rewarding or get a guide, preferably one that'll carry you up too, saves all the effort
Most of all enjoy the adventure