Here are some pictures of my yard to give an idea of the situation!
Picture of the right side of my yard. All the new construction (houses) are behind the trees.
I had no idea about this app, this is so much better than what I was using. Thanks for mentioning it!
There are some outdoor wireless mesh systems, but it is a limited selection, and you would be dealing with the same limitations with regards to the walls impacting the signal. Your internet might be slow enough that you wouldn’t notice the difference, but otherwise, you would be better off boring a small hole and fishing an ethernet cable through the wall, then seal up the area around the cable and mount an outdoor AP. You should use flooded core cabling, of course. Powerline adapters might work, but a quick search on Amazon doesn’t return any that are designed for outdoor usage.
Of course, if you run a cable out there, make sure to leave some slack drooping down before going into the device to help prevent water ingress.
No problem! I stumbled upon it in the Android store, thingy.
This is where the internet is annoying, if you were local, I’d come over and do it for you! I wonder if you can drill through one internal wall at low level between dining and kitchen/living. Then get a thin kid to simply drill and then pull the cable down from that area, down to your root cellar and towards the porch/smoking area. I’m guessing the deck itself isn’t steel, so you can even try mounting it to the underside of your porch if you don’t want it visible. Unifi and others do waterproof AP’s. Only a thought, and keeps it away from being mounted on steel, which I think won’t help the wifi…but I’m only assuming that based on experience of small amounts of steel.
Nice yard, like you say, pity about the houses - at least they’re hidden!
@Flaming_Globe good reminder about leaving some slack drooping to help prevent water ingress. I tend to forget little details like that. I was thinking of creating a custom cover made out of plastic for the device to help protect it from water ingress.
No, the deck isn’t steel; I plan to mount the device underside of the porch roof; my wife would want the device invisible; I don’t care. Thanks for the offer to help me with this project, but as you probably can tell, I live somewhere in the eastern part of the United States; it would be quite a far trip to install two ethernet cables.
Outdoor APs typically have some way of securing cables from water ingress (Linus’ video on Ruckus stuff when he mounts the T710 shows this), but you should always add the droop just in case.
Yes, they’re like that.
If you were a few miles I way, I’d do it - but you’re probably 4000-6000miles away!
Best of luck with it all 
Thanks for reminding me about leaving a loop for water to drip away from the device. I got some good news. I convinced my wife; She gave her blessing for an installed wired AP underneath the porch roof. By showing her the advantages of installing an outdoor AP, she OKed the project with only two requirements. First, I got to finish a related project. Second, The AP can’t stick out like a sore thumb.
Now while I got @ChrisA attention, it’s time to reveal what the related project is, and since a picture is worth a thousand words.
You might be thinking, what does this picture represent? I will tell you. This picture shows my crude attempt to connect my Networking Lab and my private network (meaning only I use it, not the kids or wife) to the great internet. I started this project on September 16, 2020, and as you can see, there are a few problems with it. The first disadvantage is the windows have to be open a crack. Second, the cable I used isn’t rated for outdoor use; this is the second disadvantage. Finally, I know someone will point out instead of running your wires out the windows, why not drill a hole in your second-floor office wall, fish the ethernet wires to the dining room wall, and be done with it—the problem with that plan is the walls don’t consist of the same material used today. They consist of materials that are very hard to find and require a skill level a do-it-yourself person wouldn’t have, so if the wall gets damaged while doing the project, a costly contractor will have to fix it. I have to go to bed now. I will have some questions @ChrisA can help me with.
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Congrats on the approval.
My, that’s an interesting solution you have there - but honestly, if it work, it works. I’ve used indoor cat cable outside (naughty me), firstly to get me out of a jam, but also because it would have been easy for me to re-do the run in the good stuff. Worked fine.
As for yours, look forward to your questions It’s nice to see American construction close up, timber builds aren’t something we see over here in the UK (Weather).
It was easy to get approval once I showed her how much money was wasted by having a window open a crack.
The cabling you see going outside is rated for indoors; when I implemented Project A, it was winter. Unfortunately, I didn’t have the tools to terminate the cable properly, and it was hard to find outdoor-rated cabling. Hence, I went to Microcenter and purchased two twenty-five feet of already-ended patched ethernet cable. Now it’s time to finish Project A by replacing the cabling with the correct type and installing outlets inside the home to close all the Windows.
As you can see from the picture, I am trying to install a junction box on my office window jam but have run into a snag; my drillbit will only drill the hole 4 inches deep and will not go any farther; I think I need a particular drill bit because I think I need to drill through steel. Do you know what type of drill bit I would need to go through steel? By the way, I have required the correct tools and cable to finish this project. So the only thing I need is a new drill bit that can drill through steel and the suitable diameter for the new drill bit. I thought the correct diameter would be one-fourth inch, but I now think that would be too small to push the wiring through.
Money does indeed talk 
It’s just a thought, but do you have sash windows? I only ask because the very last thing you’d want to do is drill through the cheeks, as you might end up snagging the cable on the weights. As far as I know, America doesn’t commonly adopt that window type, but I’d be remiss if I didn’t mention it.
Normally your local hardware shop will sell the right steel, over here we’d get an “HSS” drill bit, I do find it highly unusual that you’d have to cut through much steel. Are you in tornado alley perhaps as that might explain reinforced windows? You might want to see if you can get a camera or similar in the hole that you’ve already drilled, also see if you check the overall thickness of the external wall to gauge the length drill bit you need. I’ve got multi cut (timber/steel) drill bits that are 16 inches long, but that’s only because over here that’s just a little over a typical wall thickness (13 inches). If it’s not too late (which it might be), when drilling from the outside, tilt the drill up slightly, so that if water does penetrate, it’ll run back out, outside.
5/16th is probably a safer bet, just over a 1/4 inch - a similar gauge as a 13 amp electric cable that goes into something meaty, like a space heater or kettle. It’s ideal to only drill as thick as you need, to save on filler and prevent bugs getting in. Sometimes you can just find a piece of wood, drill it with a known drill bit size and see if your cable will comfortably go through it without snagging.
If you’ve got a weird amount of materials and voids, you might do well to get a wooden stick that you can attach the cable to, to then pass it through the wall.
I hope that helps, do come back to me with any follow up
@ChrisA, I Just thought I would update; I have sash windows (found out the hard way). I drill to the edge of the bottom pully. Unfortunately, the metal I was hitting was the edge of the bottom pully. So I have to find a different place to put my outlets. I probably will drill my holes somewhere under the window sash; I need to figure out where the electrical wires are in the wall before doing any more damage.
Oh dear, I had hoped I was wrong 
Under the sill is generally safe, as no electrician would want to install cables there. Not directly under the sill though, as there might be some weather protection, but an inch under should be fine.
May the force be with you
@ChrisA Another update I think I found the perfect spot for my outlet in my office. However, the second window on a different wall under the sill has damaged plaster, which I need to repair. There are 4 feet by three feet area. I need to remove the plaster to fix the damage. I can see there aren’t any electric wires in that area, and I thought I could attach my outlet to the exposed wood. If the sun comes out today, I will take a picture of the site and upload it to get your thoughts.
That sounds like a good plan, especially if the plaster needs repairing anyway, you might even be able to cover some of the damaged plaster with the pattress box you were going to use. Look forward to more pics
@ChrisA unfortunately, this project has been put on hold until next spring; my wife has removed her support because of the error I made with my office windows sash. In the spring, I will be hiring a local contractor to do some other work on the house, so I will have them do both projects. Since spring is a few months away, it will give me time to research which access point manufacture I will use. Over the Thanksgiving holiday, I will be installing new insulation and rubber gaskets to protect the ethernet cables for another five months. I will be taking more pictures. Hopefully, my new plan will allow my network to survive another winter.
Not to worry, I’m sure you’ll gain her confidence over the colder season. I’m sure the contractor can do some drilling for you at the same time, ideally he’d have electrical knowledge (so as not to go through anything sparky). If you’re not often ‘walking and on screen’, a cheap Access Point would do the job, would just mean you would be separately connecting to it while you’re outside.
If possible, perhaps get some rigid insulation and put that in the opening of the window, then once secure, drill a hole through it that’s the right side for the cable, and feed the cable through. Just a thought.