It survived! Today I pulled the winter cover, cleared minimal debris, scrubbed the liner, reconnected the pump, filter, heater, etc., and began the SLAM. Looking forward to season two!

Did you get much cold weather?
I took my 18ft x 9ft pool down for the winter but when putting it back up I had 2 small pin hole leaks where the liner had creased. Thinking it might be better to leave it up next year but worried by a couple of months of sub 30F temps.
 
London winters (and even Yorkshire winters, of which I experienced seven) are milder than Maryland winters. Here we had many nights in the 20s and more than a few in the teens throughout January and February, which was enough for the layer of ice to grow almost thick enough to reach down to the discharge port, so perhaps we dodged a bullet, IDK. Opening sure was easy; today the chem levels already were perfect and the water temp was in the 70s so my better half couldn't resist a first swim!

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@jseyfert3 leaves his intex up, uncovered, through our harsh Wisconsin winters. Perhaps he can chime in, but he hasn’t reported any issues.
I've got a 26' round Intex. Been up for two winters now. Set up in June 2020, it's now starting it's third season. The dual outlets to the filter I plugged with the black "top hat" plugs that came with my pool from the inside. I unscrewed the filter grids on the inside of the pool, unclamped the hose, and while holding the hose on the outside pulled the filter grid mount out of the rubber hose stub piece that's welded to the liner. Then I inserted the plug from the inside of the pool. Once done, I removed the hose from the outside of the pool.

I only did this once actually, in summer of 2020 after I added a skimmer and stopped using these outlets and exclusively used the skimmer. Plugs have been in place since, no leaks, through two winters.

For the rest of winterization I removed all the hoses and valves. Valves all went inside. Hoses in the outdoor chest. I took the pump inside though in theory it's fine to leave outside. I left the sand filter outside with the drain plug out and the 6-way valve in the "N" position, with all hoses removed.
full


Only "issue" I had was related to the drain plugs. At least on mine, on the inside of the pool there's a flap plug, and on the outside of the pool there's a twist on cap. Some water leaked into this and popped the cap out by a thread, and it was dripping water out of the pool. This is a concern as the ice layer dropping from water draining could snag on the outlets and tear the pool. I was a little worried for a bit, but I was able to tighten the cap up on a slightly warmer day and the leaking stopped. It did not return the rest of the winter.

It may be best to make sure those inner flap plugs are fully seated, then remove the twist plugs from the outside of the pool, to prevent this from happening. That could be worse though? Not sure. At the very least, I'd recommend removing the twist plug and making sure there's no water leaking out of the flap plug. If no water is leaking out, the twist plug can be replaced and it shouldn't cause any issues since there won't be any water in the space between the two plugs.

I wish they weren't there at all to completely remove this risk, I use a submersible pump to do the partial drain for winter anyhow.
 
The dual outlets to the filter I plugged with the black "top hat" plugs that came with my pool from the inside. I unscrewed the filter grids on the inside of the pool, unclamped the hose, and while holding the hose on the outside pulled the filter grid mount out of the rubber hose stub piece that's welded to the liner. Then I inserted the plug from the inside of the pool. Once done, I removed the hose from the outside of the pool.
I left the dual outlet grid filter mounts installed in the liner and, opting to leave the pool full rather than partially drained, confirmed that water pressure was adequate to hold the "top hat" plugs in place beneath the grid filter caps. I also left the inlet assembly in place with its valve closed.

For the rest of winterization I removed all the hoses and valves. Valves all went inside. Hoses in the outdoor chest. I took the pump inside though in theory it's fine to leave outside. I left the sand filter outside with the drain plug out and the 6-way valve in the "N" position, with all hoses removed.
I did the same but left the purged pump in place with the 6-way valve in the"closed" position. In other words, I did the absolute bare minimum and encountered no problems whatsoever. Any water that accumulated on the cover was supported by the pool water beneath, and almost no debris made it into the pool, so opening was a breeze! I will do the same next winter.
 
I did the same but left the purged pump in place with the 6-way valve in the"closed" position. In other words, I did the absolute bare minimum and encountered no problems whatsoever. Any water that accumulated on the cover was supported by the pool water beneath, and almost no debris made it into the pool, so opening was a breeze! I will do the same next winter.
Yeah it’s just as fine to leave the pump out. If I did it, I’d leave the hose attached from the filter to the pump outlet to keep rain/snow/sleet out of the pump, keep the cover on the pump basket, remove the inlet hose, and leave the pump basket drain open (I’d probably remove it entirely).
 
I've been asked for my opinion on the size of this pool, which looks huge in photos with only my wife swimming (laps!) in it. The most we have had in the pool simultaneously is ten, none of whom felt it to be crowded, and it exhibited no signs of stress with tweens jumping around and playing ball. Here is a photo of seven during a hot evening last August:

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We are hosting visitors this Memorial Day weekend and just finished moving some tropical plants down from the house. It looks nice, but I am afraid they will be damaged by summer storms, hungry deer, etc. Perhaps it would be best to install some realistic looking artificial palms or similar. Examples and sources would be appreciated!

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Also, I am [predictably] underwhelmed by the flimsy pool cover reel (my review with photos is posted here) and contemplating DIY options after finding no retail alternatives without complaints of sagging or failure. Perhaps something sturdier could be assembled using 2” EMT conduit (assuming I am unable to find aluminum irrigation tubing) and the old SUV hub bearing assemblies I have in the garage (essentially pillow block bearings, assuming simple saddle mounts would be inadequate). Searching this forum revealed some ideas, but none that I believe will meet my expectations. Thoughts?
 
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Also, I am [predictably] underwhelmed by the flimsy pool cover reel (my review with photos is posted here) and contemplating DIY options after finding no retail alternatives without complaints of sagging or failure. Perhaps something sturdier could be assembled using 2” EMT conduit (assuming I am unable to find aluminum irrigation tubing) and the old SUV hub bearing assemblies I have in the garage (essentially pillow block bearings, assuming simple saddle mounts would be inadequate). Searching this forum revealed some ideas, but none that I believe will meet my expectations. Thoughts?

I have been happy with this reel on my 24’ pool.

Since yours isn’t as wide, the 3” tube model might work for you as well.

It won’t mount to your soft side pool, but I mounted mine behind my pool on 4x6 posts. It works well for my pool which is round, but I think that it would work even better on a rectangle.

You can see mine in the background of the below pic:
 
I remembered that my reel kit included surface mount brackets as well, so for now I decided to use them rather than the flimsy, broken, plastic, top rail clamps. The tube of my Intex XTR pool has an O.D. of 2-1/4", which is close enough to the 2-3/8" O.D. of 2" EMT conduit and chain link fence terminal posts, so I modified four brace bands (~$10 total, but may have to replace with something stainless if galvanized doesn't tolerate proximity to or the occasional splash of chlorinated water) to serve as open clamps to which I mounted deck lumber as a base. It works great (the length is key for leverage), and when the next part of my reel breaks, it will be easy to mount something far more robust (DIY if not one of the GLI models recommended by @cowboycasey and @magiteck ).

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I also zip-tied to the leading edge of the cover some 1/2" PVC pipe wrapped with thin pool noodles so it is easier for one person to pull it out straight and without submarining.

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Lastly, I switched off the solar heater!

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I noticed in one picture your ladder was removed. Was that for access control? If you want a better ladder, I got the Confer 7200 which is much sturdier than the stock Intex (which is so flimsy). Access can be controlled by sliding the Roll-Guard down and locking it, if desired. This leaves the exterior stairs completely covered so the ladder cannot be used.
 
I had removed the ladder temporarily to scrub that side with the brush and to clear debris beneath the legs with the net, but I appreciate your suggestion as the stock ladder indeed feels flimsy and inspires little confidence, especially when older folks enter and exit the pool. That Confer 7200 looks super stout, but according to the manual, "Ladder must be attached to pool frame - not for use on soft-sided/inflatable pools." Presumably much of its stability comes from bracing to the top rail, which I learned how to do when remounting the pool reel, so perhaps I'll try that approach with the stock ladder first. Alternatively, step and ladder models like this one seem less intimidating (I would put the steps outside and the ladder inside).

51e68b3YiML._AC_SL1000_.jpg
 
The far corner (as seen in most of the photos I've posted) always has been about an inch lower than the rest of the pool, so today I added a second layer of deck boards to the adjacent supports. After reading posts from owners of round pools who successfully used a jack to lift the top rail where the perpendicular supports attach, I used my tractor to lift the top rail at the same angle as the supports (up and in) to achieve the same effect for this rectangular pool. Here are some photos (a combination of the clearest from each leg):

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