Have you explored the city/county GIS services? Many of them have these tools (along with a lot of other useful data) and measurements persist until deleted.
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I didn’t see that option on the county GIS, but it was really glitchy and slow when I was on it looking at soil stuff. I’ll look again, thanks!
It will not give you the areas* but I have had good luck just using something like Bluebeam or other PDF writer program for stuff like this.
Once you decide which layout you like best you can then go play with the areas in the calculator tool.
*If you know the scale of your plan, you can get areas and such in bluebeam, I am assuming you do not have a scale for your aerial view.
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Aw bummer, yeah they’re not all great.
This tool looks to allow multiple areas at the same time, although it doesn’t work on my phone:
That’s working great, thank you!
More advice needed -
Would you allow your horses to share a fenceline with neighbor horses, if they looked well cared for? I’m going to put up my own electric in case theirs fails, but can I butt up against their fence or is that a no no?
No no no no no. 
I’ve done it twice.
The first time, I was a very involved boarder and even lived on the property part of the time my horses were there. The owner next door was a wonderful horse person, but an awful “Karen.” It led to a lot of tension.
The second time I was renting a farm. I shared a barbed wire fence line with a guy who terribly neglected his animals. He saw nothing wrong with the shared barbed wire fence; neither did my landlord. Had I not used step in posts and electric to create an alley to further separate our horses, we undoubtedly would have had more issues than we did. At one point the horses all got attached to each other.
From a practical standpoint, the law can be tricky with shared fences. Sometimes you might find yourself financially liable for repairs or changes that aren’t related to your use. Sometimes you can’t change or modify things the way you would like without the other party being on board. Sometimes the other property owner can even claim right to your land if they can prove they were doing all the maintenance.
So I highly recommend just saying no to that. Even if you just leave a foot of space between the fences, keep it separate.
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Well poop. With 5 acres and such a long stretch, that’s a lot of grass! Noted, though - thanks for the advice!
I just saw your comment about a foot. That would be more doable, I was just thinking of the mowing complications of that.
No.
I’d leave a buffer - wide enough to ride or lead a horse w/o neighboring horse able to reach you.
Make note of the property markers.
They should be left alone.
I had a neighbor who bought the 5ac parcel just North of me driving his truck across a corner of my property 
Convenient for him until he built his house & driveway.
I put up a pile of brush in that corner, wired in place, planted some flowers & called it my Eff U Garden.
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Ideally I’d say leave a swath wide enough for a mower.
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I am not good at layouts in general, but without some sort of dimensions I can’t even begin to weigh in on whether or not it would work.
My initial reaction is that’s a lot of gates. Two I would eliminate are the “east” gate on the arena into pasture 2 and one of the gates between pastures 2 & 3, but I don’t know your reasoning for those. Gates are good, but are also often weak points where problems can arise, so you can have too much of a good thing. That cluster of them from the sacrifice area into pastures 2 & 3, while I understand the reasoning, may not even be logistically possible.
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I will third (forth?) the thought that it is best to leave a laneway, all the way around. It give you a great place to ride too.
I like your layout.
The only thought I have is that you might want your horse shelter (I assume the green square) so you can access it with out going into their actual area. It makes things like feeding and wound care easier.
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Eyeballing your dimensions mind you, I’d make the sacrifice lot bigger. Bringing it down level with the lower fence of the arena. But my native dirt drains perfectly fine all winter so my opinion might be different if I was planning on paying to surface said sacrifice lot
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That was my thought too, but I don’t know how big the sacrifice area truly is. But it looks too small for my preference.
Small can be good if you are doing expensive footing improvements. But too small can be a problem if the horses are spending significant amounts of time in there.
Bad COTH advice— I have never had a sacrifice area where my horses live in my entire life. Never once in 41 years. Not at my own farms, not at boarding farms. Now, I have worked plenty of places with them and they can be a great asset. But are they 100% necessary? Not in my experience.
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I think the answer to this question depends greatly on the conditions and set-up.
I will use my place as an example.
I live in a place that if I am not diligent about manure pick-up in the turn out, things go from fine to a mud pit quickly. Plus, in the winter my grass is dormant even when it is not buried in the snow.
My native soil gets pocked with holes very easily when the horses are doing silly horse things and the soil is wet, then it dries into a rock with holes and divots.
I made a sacrifice area so that my horses can be out, always. With footing that supports them even when we have a monsoon. It is big enough for them to be silly, but small enough I can pick it daily.
I have pasture space that we rotate thru.
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So you would back it up to the fence, and have a man door thing on it?
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It does depend on your set up. And climate/soil.
Also your standards. Apparently I have none. 
But I’ve kept horses in 5 different states, everything from pasture pets to competive show horses to breeding stock. So it’s not like I’m saying this from a myopic perspective.
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It will need to have a surface. According to the area calculator, it’s approximately 1/4 acre.
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The cost of fencing is factoring into my reluctance to leave a lane, as well. I agree on the riding part. Where I board now she’s lucky that she has hay fields on both sides of her - she doesn’t own them, but she didn’t have to leave a lane to be able to ride around her property.
