The NW of Scotland is hard - really hard. Much of it is truly beautiful but winter comes earlier and usually lasts well into what passes for summer here in England - you will need a place of shelter with adequate resources to provide heating for long periods where foraging/gathering will simply be impossible. Peat will be one of your best sources for storable fuel but you'll catch it hot from any authorities if you are found digging it in quantity.
On the back of that, you also need a reliable method of long term food storage to cover you against the same issues.
If you stay in one area for any length of time you will seriously upset the natural balance and drain the surrounding resources. In a good year species like rabbits will bread, well, like rabbits
but in a bad year (which could entail a number of factors other than harsh weather) the rabbit population can dip, which adversely effects predation and so many of those predators will be looking to share some of your other potential resources (or food stocks) themselves in their ongoing quest to survive.
One of your biggest enemies will be the wind - if you intend remaining coastal in the far NW of Scotland you will 'enjoy' more windy days than you care to shake the average stick at. When you get a storm up there it lives up to its name and can run for days on end, making beach foraging difficult. Also keep in mind that MW Scotland is predominantly cliffs
I spent just a few weeks up there with a close friend of mine some years ago near the Kyle of Lochalsh and he helped on the outskirts of a large sporting estate. His labours were in spectacular surroundings and there was never a shortage of game which, happily, he was able to take advantage of without fear of legal repercussions due to his position on the estate. He was basically what I would call the equivalent of a keeper's mate, if there even was such a thing.
He helped with the birds on the tops, assisted with the guided salmon and see trout visitors, did odd-jobs around the estate and did a lot of pest control with a silenced air rifle. He did a bang-up job with feral pigeons in cattle barns and stoats, weasels and rats around the pheasant feeding bins. Part of his arrangement was that he could also help himself to any train-kill, which is the rail equivalent of road-kill. If one of the train drivers reported a deer killed on the tracks that ran within the estate grounds he was able to go and harvest from the carcass at certain prearranged times (to avoid the daily train runs).
He had tried in the far NW for a time but came back down to the Kyle of Lochalsh area when he found the going too hard up there. From what I hear he is somewhere in southern Ireland now, doing much the same thing.
If I might make a suggestion, why not think along the lines of finding work along these lines in exchange for the use of a bothy or shepherds cottage, lodge or some-such ?
You could then live a semi-self sufficient lifestyle in comparative safety, foraging, fishing and hunting for much of your food but with the safety and security that a heated, if modest, home brings, not to mention the fallback of a support network of people who are at hand if you need help at any time - think injury, illness etc.
Often you can end up with more troubles than those you try to leave behind in an exercise like this, but with a little planning and a slight shift in your thinking you could very well make a roaring success of it.
I am fascinated by the American pioneers and, in particular, the fur trade era. On the one hand the romance of it all has to appeal but on the other the harsh realities are just that - harsh.
I think you could pull the whole thing off very nicely if you present yourself well to any prospective employers and don't look like a scruffy wanderer who has no business being on their land to begin with.
Lambing always requires seasonal, temporary staff in the early part of the year, and if you volunteered your services locally for the next year or two then you would be a useful addition to a sheep farm if you knew what you were doing. Endearing yourself to the local sheep farmers is an almost sure-fire way of finding more work or a place to 'live'.
Poaching carries severe penalties and unless you are literally miles away from anywhere and anyone, you will do yourself a huge favour by staying on the right side of the landowner or tenant.
Rabbits don't work as a mainstay diet, but clearing them in numbers (with permission granted by prior arrangement) for the local landowner/tenant usually gets your name circulated very quickly through the local area and odd jobs and other opportunities usually arise as a result. You might also make a few pennies by selling the 'crop' to a local butcher or game dealer, or the estate/landowner/tenant may offer you a small amount for them.
On the flip side, if you are caught harvesting game of any kind without said permission your name will be mud and it will go hard on you. The communities and scattered individuals that populate these areas are close knit and do not take kindly to folks just helping themselves.
I certainly think there is scope for a venture like this, but only if you approach it properly.
Key skills/requirements, as I see them, and listed in no particular order of relevance:
1. Shelter (obvious I know)
2. Firemaking - practice various methods including hand and bow drill, even practising in the dark and working 'blind'. Carry a hand drill set with you - it's small, light, reliable and takes up almost no weight. Firesteels are all well and good but proper firelighting skills are vital in the event that you lose or are otherwise separated from your normal method of starting a fire. Likewise, some sort of 'tinderbox' arrangement where you always carry a small amount of very dry various grades of tinder and possibly even some small kindling.
3. Water - gathering and caching/storing. Make sure you have containers of suitable capacity and durability, and at least two methods of sterilising your water other than boiling it, which is horribly inefficient and the resulting steam in an enclosed shelter can be a bloody nuisance in the colder months where it can cause your clothing, bedding etc to get damp and even freeze solid in a cold snap - this level of condensation can even spoil some types of preserved foods.
4. Food caching - I view this as very important if your are working within a limited season. You will need assorted dried fruits and vegetables, grains, pulses and rice can be good as well, otherwise your health will suffer. Either plan on finding a base and stocking it with bought supplies, which can be as simple as raisins, sultanas, porridge oats and long grain rice (and similar) or plan on gathering a lot of seasonal produce and process it yourself. If you do it the second way, you will need all manner of pots, pans, airtight containers, a proper oven is a big help (although not essential) and a freezer makes storage easy and practical. Meat and fish can be preserved in a number of ways, so familiarise yourself with the methods, practice them and work out which you prefer and which require the least gear, keeping in mind that unless you end up in a cottage of some sort you will only have what you can carry to.p process everything. The two steps are very different - processing and then storing - and concentrate on calorie rich foods. Rabbits are a pleasant treat if properly cooked but in terms of nutritional value you could probably do just as well by eating the pot you cook them in...
5. Resupply - you need a plan for being able to top up in the event that you run low on food, clothing, bedding etc.
6. Hygiene - this is the killer of the list. I am going to include general cleanliness as well as field hygiene. Basically if you look scruffy you aren't going to find anyone who will pay you for even casual labour. So you need a method of keeping yourself and your gear clean - the fringe benefits are that this is a great morale booster, it keeps you warmer, and reduces the likelihood of parasites.
I could mention other factors but the above would be the primary concerns in my eyes.
Keep in mind that a lot of the area you are talking about has a high risk of Lymes disease, particularly in late spring and early summer, which can be pretty nasty. I had two courses of antibiotics to get rid of Lymes disease last year and I felt like crap as a result of it - the joint pain and swelling alone would make dextrous work difficult and the fever is obviously a real danger to anyone going solo. Had I not insisted on being tested for it my doctor would never have added it to the list to be checked when he was organising blood tests - the legacy of Highland deer stalking
Also keep in mind the infamous Scottish midge which, as we all know, are specially trained by the SAS to make your life an absolute living hell without the right kit, lotions and potions
I always start by examining the obvious negatives - this may seem like a killjoy approach but once you list the most obvious and/or potentially dangerous, you can develop strategies, skills and plans to draw a line through them, and move on to the next problem. The more you do this in the current safety of your present situation the better armed you will be when you try this.
I'd love to hear how you get along - maybe part of your strategy for returning back to the 'civilised' world at some point should involve writing a book about your adventures, so add some sort of journal to your kit list and use it daily...
Best of luck, and I mean that wholeheartedly.