Welcome, and happy to hear you’re getting back to biking!
“Cross” (Cyclocross) bikes are a lot like road bikes (they use drop handlebars), but generally have gravel-friendly wheels, and tires, and have disc brakes. They are very versatile - pretty good on road, paved or dirt, pretty good on gravel. Not as high performance on road as a dedicated road bike, not able to handle rough terrain that a dedicated mountain bike could, but great for in-between. The Jake the Snake and Crossrip are Cross bikes. Actually, now that I look at their websites, the Kona Jakes are listed as cyclocross/commuter, and the Trek Crossrip a commuter/gravel bike. Trek’s entry level cyclocross bike is the Crockett. It seems the bike manufacturers are building more hybrid bikes these days.
A cool place to road ride right now is the Indigo Shores subdivision just outside Sackville. Since it’s a new subdivision, it’s got good new roads, but hardly any traffic. It’s like a backwoods ride on nice paved roads. In and out with a loop is about a 45-minute ride for me.
Probably most of us here ride mountain bikes (although a lot of us ride road too). Have you thought about trying that style of riding out? Much safer than dodging traffic on the road, and getting out in the woods is a great escape and adventure. You can probably get into a used mountain bike cheaper than a good quality used road or cross bike.
Rail-trail and park “crusher dust” trails are relatively easy rides and suitable for a mountain bike or Cross bike. Point Pleasant, Shubie Park, Sackville Lakes, Hemlock Ravine, Clayton Park powerlines, Salt Marsh Trail are all good gravel rides in HRM.
Try to avoid buying department store bikes (Walmart or Canadian Tire), or at least test ride at bike shops before buying, so you’ll get the right size and know what to look for. The quality and assembly of department store bikes are way below bike store bikes. Giant, Trek, Specialized, Kona, Norco, Cannondale are probably the biggest names in bikes. However, each manufacturer has a range from cheaper, lower quality components, to high-end mortgage-the-house practically gold-plated bikes. You can often gauge the quality of a bike by looking at the rear derailleur - it will help to estimate the level of components:
In mountain bikes, from worst to best:
Shimano: SIS, Tourney, Altus, Acera, Alivio, Deore/Zee, LX/SLX/Saint, XT, XTR
SRAM: X3, X5, X7, X9, NX, GX, X1, XO, XX
In road bikes from worst to best:
Shimano: Tourney, Claris, Sora, Tiagra, 105, Ultegra, Dura-Ace
SRAM: Apex, Rival, Force, Red
If the rear derailleur doesn’t have a label, it’s a generic very cheap component. If it says Shimano, but doesn’t have a model name, it’s probably bottom of the line SIS.