Is 5 Nights in Oban in 1st week of October too much?

It's impossible to predict the weather. It could be glorious or could be awful or somewhere in between (the most likely).

Although it does happen the 'big boats' across from Oban to Mull are more likely to keep running, as is the ferry across from Fishnish to Lochaline (as that is in the sheltered Sound of Mull).
The ferry from Mull to Iona (although very short) can get very tricky very fast. If there is weather it often runs on a sailing by sailing basis.
The boats out to Staffa are small tour boats, not ferries- they are very prone to weather- I would see those as having a high cancellation risk.
But there is more to Mull than just dashing over to Iona. There is Tobermory (aka Balamory), there is the return drive from there via the wonderful Calgary Beach. There is the little known Isle of Ulva- a sheltered Loch crossing.
Back on the mainland there is the Bonawe Iron Furnace, the Cruachan Hydro Electric Plant (very interesting), the drive down to the slate islands across the "Bridge over the Atlantic". Those are little ferry crossings in fairly sheltered water (not CalMac boats) so less likely to be weather altered.
Using the Craignure and Lochaline ferries and then the Corran narrows ferry there is the scenic drive over the Morvern peninsula towards or even to Fort William.
In October, on Option 2, is Shieldaig the best place in the area for a 2 night stay, or is it just somewhere you have heard of. What about Kinlochewe instead, 17 miles further on along the NC500- with the beautiful National Trust for Scotland Inverewe Gardens.

If the weather is rough in Oban chances are it's going to be rough on Skye as well (option 3).
If worried about the weather being rough at Oban then you're better off sticking to the mainland. But I would jump at the chance of 5 days in Oban in October personally- when the Summer crowds have gone, and it "should" still be reasonably benign.
Little love is shown for Oban on this forum- I respectfully disagree.

@isn31c Thanks a lot for such a detailed response. I absolutely understand that the weather around there can be extremely unpredictable so just trying to understand a little more. From your response it seems like there will still be enough & more to do in & around Oban even if the weather gets rough on & off. I have heard similar feedback about Oban not getting it's due from travelers in other forums & it is exactly why it's on top of our list. Another bonus, proximity to Edinburgh which is where our return flight is from. When you say .." worried about the weather being rough at Oban then you're better off sticking to the mainland" do you mean sticking to Oban or another place altogether? Not sure if you mean if we are better off going to another part of the Highlands.

I understand you said that you would jump at the chance of spending 5 days in Oban in Oct, but would you say that to a tourist (me) coming to that part of the UK for the 1st time or you'd advise them to look at other options. I would love an honest answer & will not hold it against you either ways :). We feel drawn to that region especially after having read such glowing reviews, it's hard to not consider it seriously but also want the best utilization of our time & $$! :) Would never expect anyone to decide for us but just gathering information to make an informed decision.

Re Shieldaig, it was something I read from another traveller's itinerary & the general route seemed interesting. But I will look up Kinlochewe instead if we do plan to take on that route.

Thank you again!

When you say .." worried about the weather being rough at Oban then you're better off sticking to the mainland" do you mean sticking to Oban or another place altogether? Not sure if you mean if we are better off going to another part of the Highlands.

I guess I really mean that I mean sticking to what I would call the A9 axis- in broad terms working my way up the A9 highway towards Inverness and Loch Ness, maybe working my way back down the East Coast towards Dundee and St Andrews- a derivative of Option 3 but without Skye. Hopefully Jacqui (Skye Girl) will chip in but I'm not sure how much will still be open on Skye in October.
Mardee (one of our regular North American contributors) has just done a road trip which took in the East Coast and relished it- she can give you an American (not locals) perspective on that.

I understand you said that you would jump at the chance of spending 5 days in Oban in Oct, but would you say that to a tourist (me) coming to that part of the UK for the 1st time or you'd advise them to look at other option.

A very, very hard question to answer. The key is flexibility. BUT given the chances of not getting to Iona and Staffa, in terms of getting "bang for your buck" Option 2 or 3 or some derivative of them may be the more viable option. Oban is certainly not foolish, but the other options are more resilient- that's the word. Also, while you can still walk around Kilmartin Glen the Museum is closed until "Summer" 2023 whatever Summer means. Will they re-open in August/September or wait until 2024?

But there is more to Mull than just dashing over to Iona. There is
Tobermory (aka Balamory), there is the return drive from there via the
wonderful Calgary Beach.

Finally, someone other than me writing how wonderful Calgary Beach is. Mull is worth a couple of days over Oban in my opinion. Having said that, when we were there on this week last June, our ferry to Iona was cancelled due to waves. Like a box of chocolates, you never know what you're going to get with the weather and the ferry.

Hi Addy! isn31c has given you some great advice. I was there last month for 3 weeks. I can't speak for the rough weather, but as both isn31c and Allan pointed out, ferries can be cancelled at any time during the year. Also the Staffa tours can be iffy (my tour actually went out but was unable to land). But I loved the Isle of Mull - it was fabulous! Unfortunately, I did not make it to Calgary Beach because my fear of heights led to a slight panic attack driving on the mountains to get there and I had to turn around. :) But I think most people would be fine, and that was only place I had real problems.

But I can tell you that traveling the NE coast was a wonderful experience. I did some island hopping first (Arran, Mull, Skye and Harris and Lewis) but after taking the ferry from Stornoway to Ullapool, I began my road trip. I started at Culloden Battlefield and visited Clava Cairns, then headed up to the coastal town of Nairn (beautiful town) and traveled along the coastal road.

I stopped at Cawdor Castle, then spent the night in Elgin so I could see Elgin Cathedral but also attended some Highland Games at Gordon Castle in nearby Fochabers. It was a gorgeous trip - there were beautiful scenic views of the sea in Portknockie, and the tasty experience of eating a bowl of Cullen Skink soup in Cullen.

Next I stopped at the Bullers of Buchan, an enormous collapsed sea cave with incredible views, then the ruins of Slains Castle, which was the inspiration for Bram Stoker's Dracula, and spent the night in Cruden Bay. Then continued down the coast through Aberdeen, stopping at Newburgh Seal Beach and a few other places.

I saw some wonderful things, and the drive itself was much easier than driving on the islands. That was the hardest part of visiting the highlands - the driving. Luckily in October, there won't be the traffic you will encounter during the high season (esp. on Skye) but it's still a little nerve wracking when you start driving up into the hills. At any rate, I really want to go back and devote more time to the NE coastal route. Because I spent a good portion of the day at the Highland Games, I wasn't able to stop in as many places as I liked (not that I'm regretting the Games!). So hopefully next trip. But it truly is a wonderful road trip.

Another option is to start off at the same place but at some point head down to Dufftown, visit the Spey River distilleries there and visit Cairngorms National Park. There is so much to see and do in Scotland. I really fell in love with this country. If you want, feel free to read my recent trip report: https://community.ricksteves.com/travel-forum/scotland/solo-in-scotland-trains-cars-and-ferries-and-a-wee-dram-or-two

Not much of an expert but I have been to both Shieldaig and Kinlochewe. Shieldaig is lovely, Kinlochewe is magnificent. We didn't stay in either though. We were sleeping in our little van and stayed firstly in magnificent Torridon and then on a beach just out of Poolewe (where the Inverewe Gardens are).
The drive over Bealach Na Ba to Applecross is pretty impressive although weather in October?
The drive north from there was also very impressive. At Kinlochewe there was a visitor's centre below Bienn Eighe (is it open in Oct?) and hiking trails up Bienn Eighe which were brilliant but we were there in August. Could be rough in October.
Poolewe had a decent pub that served good meals, at least it did a few years back.
Just loved that area.

Re Isle of Skye.
Beautiful particularly up north. But in August (a few years ago) it was pretty busy with tourists, particularly Portree. Maybe different in October.
We enjoyed it but were happy to wander across to the quieter Isle of Raasay for a quieter time. Probably not enough things to do and see for most but both myself and my wife loved it.

Wow! That is a lot of information to take in. I am going to read through these comments thoroughly & regroup. What a wealth of knowledge this has been. I'm new on this forum & do sincerely appreciate you all sharing your thoughts & feedback. I am probably going to come back with more questions. :)

UPDATE: Since you all have been very helpful with all your suggestions, I thought I should let you all know that we have sort of finalized our plan. Here is what we are going to do:

Days 1 & 2 Edinburgh

Days 3,4,5, Oban via Stirling & Glencoe; Overnight in Oban

Day 6,7 Isle of Mull (Day trips to Staffa & Iona, weather permitting)

Day 8 Back to Oban; Overnight in Oban

Day 9 Drive back to EDI via Loch Lomond; Overnight in EDI

Day 10 EDI Early PM Flight Back

I know we don't have enough time in EDI, but we thought we'd take advantage of being in the Oban region at a slightly off peak time to enjoy it!

Thank you again for all your suggestions!

Do you already have your hotel lined up in Oban? If not, I can highly recommend the Invercloy Guest House. While the decor is nothing fancy, the beds are super comfy and the view from the bay window is MAGNIFICENT! I could have just stared out that window all day long! Oban is wonderful.

I only did Mull as a day trip, but I still loved it. Spending the night will be even better. The ferry ride there is so much fun - even in driving rain and wind!

I was there in October as well, and while there was some rain every day, there was glorious sun every day too. It was magical.

Enjoy!

Your plan looks perfect. Weather around Oban will be very similar to Skye. 1st week of October will see some touristy places closing but still should be plenty going on. Oban will make a great base for your trip

Thank you, Skyegirl. We sure are looking forward now that we have finalized. Will come back to visit Isle of Skye another time & will look out for your advice! :)