Not the answer your want. Start with a dumb telescope and learn to navigate the stars. You’ll get better optics if you aren’t paying for all that other stuff.

The only “smart” feature that I find useful is an equatorial gear/mechanism. It turns your telescope with the rotation of the earth (or fancier ones can be set to turn with the earth plus another movement so you can track objects like the moon). Just look for that.

Camera mounts, specific lens, and filters can be great additions. None of those things are “smart.” Here’s a photo I got of the lunar eclipse the other night. I didn’t use an equatorial mount or filters because I was rushing and didn’t want to set it all up, just a camera mount, so I apologize for the quality.

Counter-point to many here (although they are very valid positions)…

Lots of people find the views from telescopes underwhelming and frustrating, especially on the cheaper end. Cheap bird optics and mounts on Newtonians and learning to collimate properly is a hassle. Dobsonians are pretty approachable but are a huge hassle at the sizes they tend to come in. Moderate SCTs are decent but at a pretty steep entry level price for a curious hobbyist.

There’s no replacing the feeling of raw photons hitting your retina, but it’s easy and cheap to get a camera sensor and capture far more detail than your retinas ever could.

Dwarflabs and Seestar have options for a few hundred bucks, they are extremely portable, they do require an app, but they’re dead simple to use to start exploring within 10 minutes of unboxing. You’ll get images you’ll want to share with friends, and with a little practice you can have print-ready deep sky nebulas. The telescope that’s easy to use is the one that gets used, and these are nearly unbeatable for helping keep the interest and motivation going.

Find a local astronomy club, look at their telescopes and enjoy the view, but it won’t be close to what you see on the web.

Not your target audience, but… Bright binoculars (10x50) have kept me happy for nearly a decade for half the price of those telescope options. I do want a telescope, but based on a small sample pool at astro parties, it’ll take notably more money to make it worth it to me.

Bino pros: cheaper, brighter, more portable, very little setup, two-eye comfort, terrestrial use, more durable, wider apparent field of view (bigger image), wider image field of view (more stars, easier navigation), prism optic to keep image upright

Bino cons: much less zoom/magnification capability for portable/affordable sizes, hard to see ~half of the messier catalog at all, and I frequently skip the tripod because ei can totally stand there for an hour with my arms holding 2lbs over my head steadily (hubris strikes again), and the combination of reduced zoom/smaller objects makes it harder to enjoy the viewss in Bortle class 5 light pollution or worse.

Pro to smart telescope: even if it’s aligned a little poorly, the tracking should keep targets in view for a several minutes. Untracked, they might only be there for a minute. Based on my experience with a ~80mm lens, ~1m long telescope. For me already being familiar and taking a dozen attempts to acclimate to the flipped image, I was able to keep it on target fairly well initially and continue to find new targets with a slight miss of the auto alignment.

I built a parallelogram mount. It’s rare for me to take it out on dark sky trips due to bulk of the mount and recliner chair, but when it’s out, the stability makes for a beautiful image. A regular tripod setup is tough to get views overhead, though a ball mount and counterweight on a 1m beam is an easy compromise

I do appreciate the one time I saw the Orion nebula from an Observatory through a ~24" dobsonian scope, but that’s a lightyear beyond my budget.