I haven't seen anyone mention it, but the 11ft one wind hammock is a fantastic entry hammock that fills majority of needs. It's around $75 usd and has everything you need to get started except a rain fly. Cheap hammock, pricey-er top quilt and under quilt as budget allows. Also would suggest Hang-Tight Gear, they make very affordable under quilts and top quilts!! https://a.co/d/01z9QJ5q https://www.hangtightshop.com/
There's a lot of good info in here already, what I would suggest that hasnt been mentioned is that you should pickup and read "The Ultimate Hang" as it details how you should setup the hammock, which is about 75% of the comfort battle. As far as a particular hammock, I'd really suggest the OneWind hammock off amazon here. It's a great all-round hammock and is cheap enough where if you find you don't like hammocks, you're not out hundreds. I recommended it to a few friends and honestly it's a great hammock. You just need to adjust the ridgeline yourself to the proper length. Built well and compacts down with all the things you need. Also consider, if you want to camp in under ~70° you will want an underquilt, which goes below your hammock and keeps your back warm. Typically people get 20-40° rated UQ's and use them all year round. I just bought some HangTight underquilt and quite enjoy it, and it's a good price.
I suggested my friends get the 11ft one wind hammock and I was honestly super surprised with the quality and features. I would highly recommend anyone looking to get into hammock camping this hammock, the width and length is great for the majority of people and has great features. My only complaint is that you need to adjust the ridgeline before using it, it's adjustable but is not the correct length out of the package. For new hangers, that's not something that's clear or intuitive.
Close to your (soft) budget I doubt you’ll find better value than https://a.co/d/dNmllEm . Not sure how Amazon prices work in Canada. Note that does not include tarp that would make a more complete setup. For really anything under like 20°C, especially if any wind, you get surprisingly cold overnight. Sleeping bag does almost nothing where flattened by your weight. Cold Butt Syndrome. Best remedy is an underquilt. Same company OneWind makes a cheap one good to at least 10°C. Underquilts breathe, unlike pads. If you really think you want to use a pad in the hammock, you really want a double-layer hammock, so you can insert pad between the layers. Otherwise trying to stay on top of pad as you move around is not a good time. OneWind also sells a double-layer hammock suitable for use with a pad. I don’t have direct experience of OneWind. I’m going by spec/design matched to China-made low price point, and testimonial of others whose opinions seem solid. Expect some quality control irregularities, but for the price… At much higher price and quality are the so-called cottage vendors of US. I know of only one Canadian maker with high reputation, but haven’t researched hard: Little Shop of Hammocks. Hennessy Hammock is another decent-value brand. They used to be super innovative, but just kind of stopped, apparently to focus on lower prices and broader distribution, while the “cottage makers” have continued to innovate design fundamentals Hennessy pioneered. Onewind, you could denigrate or applaud as a Chinese cutthroat-price heist of many cottage maker design refinements. I’m hammock crazy and thus not very price sensitive. I love my Warbonnet BlackBird XLC setup with Wooki underquilt, WB topquilt, lots of accessories from several other companies.
