San Diego! We really like that city. So much to do in all the different areas, which have different vibes. Downton, La Jolla, Pacific Beach, Coronado. Close enough to each other, too. Easy enough flight.
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Florence
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I of course love San Diego because it was my dream relocation location.
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Has to be in US, though Florence sounds great.
I also know that a lot of cities, mine included have begun to limit vacation rentals. They want the housing stock to stay in the full time renting pool.
San Diego is similar to where we already live.
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There are beautiful places in Oregon. Kid and her friends went skiing near Bend and fell in love with the area.
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Oh here is a good one! 
And the price seems decent. 
https://www.redfin.com/HI/Kapolei/92-1479-Ali-inui-Dr-96707/unit-31F/home/88573484
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You could compromise on Florence, OR (home of the famous Exploding Whale)
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I’ve been to Florence Oregon and it is beautiful.
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One thing with Hawaii is the ability to have a legal short term rental. It’s sometimes hard to find that out from the listing. Timing looks like we will need to find a replacement in Sept or October. Hope prices drop by that time or at least inventories increase.
Any Hawaii realtor should be able to tell you which listings can be a legal short term rental and which cannot.
You should be able to look up the property’s STR permit status.
I’ve always enjoyed coastal Carolina, both N and S. Topsail is a favorite for us. North Topsail is still fairly quiet, especially if you have your own beach access, while still having the amenities of Surf City/Emerald Isle/Hampstead/Wilmington near by.
We’ve only been to OBX a few times. I like that it’s even quieter (at least the places we’ve stayed), but amenities can be hit or miss depending on where you are along the string.
Seabrooke Island in SC is amazing. We’ve gone there a few times and I love it! My only “eh” is that unless you have one of the very few homes w/ beach access, you’re walking a good bit to get to the beach. Fine for us now, but would think that would be less than fun w/ grandkids later on.
Sadly, I think many of these places will cease to exist in the next few decades.
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This is a serious dream for me…
Background: I wish to become a doctor (in HS right now) in the UK (Sheffield, Gloucester, Edinburgh area). Additionally, I have fallen in love with a rare breed of sheep called Swiss Valais Blacknose sheep. They are each about 5000 USD. They are the cutest things!! They are quite picky and require rocky, grassy land.
Dream: In Scotland, by Glasgow, there is a beautiful park called Loch Lomond and Trossachs. One of the prettiest parks known for it’s clear lakes, you can buy large plots of land right on the shore. I would then build two houses and a barn. One house would be around 4,000 sq ft and one would be around 1500 sq ft. The larger would be used for an AirBNB while the other would be a sheep breeder/ sheep enthusiast who would take care of the sheep and get them ready for sale. The breeder would be paid a bit less as I would be granting him free lodging. (may also just hire him to come around daily) Therefore, the guest would be able to explore the park while enjoying the sheep. There would be around 8 ewes. Every spring, a tup (castrated ram) and ram would be borrowed for baby lambs.
Estimated cost: 500,000 USD
Better start buying them lotto tickets 
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If you’re looking for something “different” than San Diego, how about Cannon Beach in Oregon? Or the Seaside area. We liked Hood River Valley also, but I suspect Cannon Beach is more popular. Or the Willamette Valley region - they have great wines.
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Condos in Seattle apparently went down in price from 2018 levels…
Black nose sheep are between 1k-10k, not 500k. Considerably less lotto winnings needed.
First of all, those are the cutest sheep. Ever.
But @gouf78 I think you misread the OP. S/He said $5,000/sheep, which fits in with your $1,000 - $10,000 estimate.
underneath the picture though it says 500,000 USD. Or maybe that’s the cost of the land, sheep, homes etc.
Yes, I think that was the total cost of his/her dream life.
OP I totally empathize. I will say this: hold on to your dream. I was a lawyer, and now I have a farm boarding retired horses (my dream). It can be done. Definitely marry the right person though. 
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No. The plan is to have a nice barn and a house on the land as well. The house would be meh 3000 sq ft. It would be a Vrbo or AirBNB. I found some land for around 180000 euros right by a Loch near Glasgow. It is in the Loch Lomond and Trossachs National Park
Some other places I am considering as well…
Lake District, Sheffield:
Peak District:
Just imagine having a sheep farm/vacation rental in one of these parks…
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