The one most people should buy
Sky-Watcher Heritage 130P
$305
130mm (5.1 inch) tabletop Dobsonian, 650mm f/5
The most telescope you can buy for the money, and the one most likely to actually get used.
Aperture is the spec that decides what you can see, and 130mm of it for around three hundred dollars is the best ratio on the market. The Dobsonian mount has no motors, no alignment routine and nothing to fail: you point it at something and look. It collapses small enough to carry outside in one hand, which matters more than any optical number, because the telescope you leave in a closet shows you nothing.
The catch: It sits on a table, so you need a sturdy one. The collapsible tube lets stray light in and drifts out of collimation a little more often than a solid tube, and the helical focuser will not hold a heavy eyepiece or a camera.
If the budget stretches
Sky-Watcher Heritage 150P
$355
150mm (6 inch) tabletop Dobsonian, 750mm f/5
Fifty dollars more than the 130P for a real jump in light grasp. Buy this one if the budget stretches.
Same design, same simplicity, one size up. Six inches of aperture is where globular clusters start resolving into individual stars and the brighter galaxies stop being smudges. If you can afford it and you have a table to put it on, there is little reason to buy the 130P instead.
The catch: Bigger and heavier than the 130P, and it shares the same open-tube and focuser compromises.
If you want a tripod, not a table
Celestron Inspire 100AZ
$330
100mm refractor, altazimuth mount, full tripod included
The pick if you want something free-standing rather than something that needs a table.
A refractor needs no collimation and holds its alignment essentially forever, which suits people who want to set up and look rather than maintain equipment. It comes on its own tripod, so there is no hunting for a surface at the right height, and the smartphone adapter built into the lens cap is more useful than it sounds for Moon photos.
The catch: 100mm collects less light than the 130mm Dobsonian at a similar price, and refractors of this class show some colour fringing on bright targets like the Moon and Jupiter.
If you would rather look than search
Sky-Watcher Virtuoso GTi 150P
$545
150mm tabletop Dobsonian with GoTo tracking, driven from a phone
The Heritage 150P with motors, for people who would rather look than search.
Finding faint objects by star-hopping is a skill, and it is one some people enjoy building and others find infuriating. This is the same six-inch optical tube on a motorised mount you drive from your phone. It also tracks, so an object stays in the eyepiece while you fetch someone to come and look, which is the single biggest difference when you are showing the sky to other people.
The catch: Motors mean batteries and an alignment routine, and it costs a hundred and ninety dollars more than the manual version of the same telescope.
The one people wish they had bought first
203mm (8 inch) Dobsonian, 1200mm f/5.9
The scope people wish they had bought first. Worth saving for.
Eight inches is where the hobby opens up: the Orion Nebula gets structure, the Cassini division in Saturn's rings is obvious on a steady night, and dozens of galaxies become real objects rather than rumours. It ships with a decent finder, two eyepieces, a laser collimator and a cooling fan, which is most of what you would otherwise buy separately in the first year.
The catch: It is a large object. The tube is around four feet long and the whole thing is roughly fifty pounds in two pieces. If you live up three flights of stairs, buy a Heritage and be honest with yourself.