I currently live on a very small island, and previously lived in a mid-sized town for 3 years (near Thessaloniki), and I also have lived in (and still commute with) Athens, so I may have some advice, especially as relates to the small island thing because that's where I am now (physically and just as importantly, mentally!). Many folks on this board have a lot of experience in the larger cities (Athens, Thessaloniki) as well as some different islands.
Your list is quite impressive for a 20 year old, having a good work ethic will definitely be something that Greek employers will be grateful to get their hands on, especially outside of the cities. However - that is not going to guarantee that you find a job! Read on...
As far as which of those skills will be most needed - if you are looking into living on a small island (for the higher quality of life and the educational advantages - to which there is also OF COURSE a significant downside, which I will get into in a minute) - you would probably not find work in sales, web design, food, media EXCEPT in the summer months - and unless you are the owner of a business, summer income is only enough to survive on in the summer - it will NOT carry you through year-round - that luxury belongs exclusively to the hotel and restaurant owners!
Be careful when you think about relying on your construction skills because the smaller islands like mine are well stocked with very inexpensive SKILLED construction labor and I find it very unlikely (but this is just me stereotyping here) that a UK citizen would do construction for the pay rates that these men will do, because they are generally here as economic refugees (okay that is not the proper term but I cannot think of it right now). In other words, they are willing to work for peanuts (as we Americans say) and don't demand annoying things like health coverage or decent hours. (Here on my island, they work all days of the week, yes even on Sunday, I know because it is annoying to me to be woken up by circular saws outside my window at 8am on Sunday morning!). There is also no job security whatsoever in this field, which is why it is to their advantage to be highly mobile - easily moving from one island to another - this is not easy to do with a family that has invested in a particular school/area. Construction in the islands is pretty big business in general but is taking a hit with the economy along with everywhere else.
Web/graphic Design - this would be something you might look into - however, without knowledge of Greek (sorry, forgot to ask this - do you speak/write Greek?) you will be forced to work with a Greek colleague for all Greek sites and this will cut into your pay. As much as it is tempting to say this is work that can be done from anywhere (i.e., clients in Athens, you on a little island) keep in mind Greece is very much a face-to-face place and you will need to be able to meet your clients directly if you want to build up a client base - this is just the reality of doing business in Greece.
If you want to get into IT support and such - keep in mind that a typical highly skilled and experienced IT worker in Greece (with diplomas) will make up to about €1000/month and that is with several years experience working with the same company. I dated a man in this field in Greece; he worked for the same company for 4 years and made about €900/month and was considered indispensible and a very good worker, so do not expect to be making a lot of money in this field. Also you REALLY need to speak Greek in the field of IT in Greece, although some knowledge of English is expected, Greek (including technical Greek) is a must.
Hairdressing - this is going to be a HUGE challenge to build up a client base if your fiance is not Greek (is she?) or Greek-speaking - this just goes to the culture here. However, there could be a market if you went to the right place (like a "pretty island") for a British wedding hair stylist - someone who could take care of hair and makeup and manicures for ladies who travel to Greece to get married here - this is actually quite a lot of people, and the tour companies have wedding packages that they use - if she could get into something like that, working for British companies (I don't actually know if they employ people in this manner, I'm sorry), she may be able to avoid some of the difficulties of being a truly LOCAL hairdresser (I don't know if it's even legal to be a hairdresser in Greece without holding a Greek hairdressing diploma - I mean I really have NO CLUE but I would suspect you would need to get this diploma or a recognition of a British diploma of the same type - this will need looking into).
As far as schools go - any specific information you need, you can ask me and I will ask my fiance; he has taught in Greek schools in Athens, Zakynthos, and the Cyclades. I am sure he will be happy to help!
As far as where... well if you've only narrowed it down as far as "small islands and medium towns/cities"... that's not specific enough for me to help, but if you do think you'd like to try living on a small island, my experience is with the Cycladic islands, and I would give you the following warnings based SOLELY on my personal experience.
- small islands usually have an ENORMOUS flux of population. Our island goes from 15,000 people in the summer to 300 in the winter. This has a lot of implications, including:
- it is easy to find cheap accommodation (renting) in the off-season (assuming you arrive before everyone disappears) - but you will either get kicked out in the summer (so the higher-paying tourists can live there instead) or you will have to pay going tourist rates, which can be around €120 or more/night, especially if you will be needing multiple bedrooms (we have 1BR and pay €240/month, would pay €100/night in summer if we didn't leave, which we do).
- living in a place with only 300 residents means: infrequent ferry connections with larger islands and the mainland, inadequate medical care (some of the islands do not even have a pharmacy, instead, the clinic has the basics, and a pharmacist comes by once or twice a week from a larger island), very few dining-out options (we have about 4 year-round tavernas on our island), much higher prices for groceries (we pay about 1.3-1.8 times as much as what I am accustomed to paying in Athens with of course NO variety), no farmers' markets or reliably decent produce available (you get what's available and you eat it when you get it, but you can't pick and choose - we went about a month without garlic, for example); we don't even have a bank (just an ATM) which can make about 9 million things more difficult than necessary, there is no entertainment whatsoever
- It also means: there is literally NO traffic, you fill you gas tank 4 times / year, everyone on the island knows you and will help you out in any time of difficulty, when the ATM runs out of cash they give you your groceries on credit (not credit card - I mean they write it down in a little book and you pay when you can), there is ZERO crime, the school teachers are deeply invested in the success of each and every student, the air is so clean your lungs will be in heaven, the arrival of the ferry is a social event to look forward to, you start watching the "beaufort" weather reporting with actual interest, you try and try and you CANNOT spend money because there is nowhere to spend it except the grocery store, there IS internet (although it is kind of spotty - sometimes it goes out for a few hours at a time, same with cell phones, same with electricity), so you are not totally cut off.
We LOVE it. For two years. After our second year, we are getting the hell away from here. But with amazing memories to last a lifetime. There are always pluses and minuses, just think about what your priorities are
(Now, I also live on one of the tiniest islands. A place like Santorini has 2000 residents in the winter and has a lot more going on.)
Medium sized towns have very little of a downside. I'll think about it because I have a lunch date and get back to you.
