I love having a pool! And a hot tub! I've been using the hot tub since March! It takes little time to heat up. Now that the cold fronts have ended, I heated up the pool last weekend once and it stays warmer! We are expecting temps in 90s next week.
We put in a pool in 2000 at previous home. Kids were younger/teens. Thought it was for them, but we used it the most. An outside bathroom was an essential alternative to dripping through house to bathroom. The "cabana" had a sink, tiled surface, and a fridge. But we were in the country, so mice, etc. were a small nuisance. Also, had 2 oak trees that provided shade in afternoon. They dropped pollen in the spring, and leaves in the fall!
Then we moved to the city for a few years, knowing it was temporary. No pool. Well. the hot tub liquidation commercial came on tv. Let's just go look... They delivered and set it up! It was before Covid and cost around $6,000. Worked great for the small backyard we now had. We could drain it and refill it easily. It stayed clean with a cover that folded back. It worked, but it was not a pool. My mantra was, "My next house will have a pool".
Now, in our new home/ranchette, we have a pool with an elevated hot tub that flows into the pool. Lovely, relaxing water feature when rocking on back porch. No trees around it to drop stuff in pool.
You live near Chicago? How many days will it be comfortable to be in water outside? How do you plan to use your pool? Swimming laps, soaking in the sun, ...
The hot tub might me a viable option.