Hi Tyler, welcome aboard!!
Was your Bissell canister the red Bissell Digipro with power nozzle by chance? I was always curious about how those did. They've been on the market for many years and Bissell hasn't really made any changes to it that I know of in that time.
If you're replacing a canister, wouldn't you want to stay with a canister. After all they do great with car interiors, steps, carpet, bare floors, versatile to go under beds, easy to manuever, tend to be quieter and so easy and fun to use. Having little budget you may want to look to the lime green or orange Kenmore canister. Lately they have been going on sale for as low as $99. If you want the Kenmore original style tool set, better plastic and a few other upgrades then you could look at the red Panasonic MCCG902. There's a few on eBay right now starting at $115. Good suction, great power nozzle, universal fit hose end will fit many other manufacturer tools.
Going from a Bissell to a Kirby I think you'd find the Kirby very hard to use and definitely MUCH heavier. I personally am not a Kirby fan cause I'm switching back and forth from attachments to carpet, I'm not wild about the self propel, they're quite heavy and personally I don't find they groom a carpet as well as many other vacs I've used. This is strictly my opinion from using vacuums for over 20 years and cleaning houses for over 18 years, I am 30 years old. You'll hear many other members on here completely disagree with that.
Orecks are ok for low to medium pile carpet. Even at medium I'd look to something else. David Orecks ads claim over 100MPH and high RPMs for agitator but CFMs and small fan are where it suffers. Air can go through a drinking straw at 100MPH but the volume of air coming through the straw is still minimal. That's where CFMs come in. In addition I've had allergic reactions to all 4 Oreck uprights I've ever used, to include XL2000 Commercial, Dual Stack commercial and 2 Oreck Ultra XLs. I did try one Oreck XL 21 briefly after fixing it for a friend and was unimpressed with performance I also think they're loud. On the other hand I like Oreck's power head canister's the former Dutch Tech line with Wessel Werk EBK340 power nozzle and the new red Quest Pro isn't bad.
Riccar/ Simplicity are essentially the same and are great brands. I have a Riccar 1700 canister that I'm happy with. A neighbor of mine has a Simplicity that theirr happy with. They are USA made, they tend to have metal brush rolls, metal bottom plates, rubber coated wheels, tremendous airflow, easy tool conversion. They are pricey but I think they're worth it at $800 or below. Some vac shops have refurbs and eBay can bring some up. I like their uprights and canisters.
I would also recommend the Royal SR30020 canister. Also check ebay. You may be able to find yourself a Miele or model listed above at low price. I would definitely go with bagged over bagless. I personally would do canister as well regardless if you're doing wall to wall carpet or a mix.
A lower priced but still good cleaning upright if you want that route would be the Hoover bagged WindtunnelMax or T Series bagged. I've heard good things about those.
Keep us posted.
