Bikes are a bit like stereo equipment, you get much better bang for your buck by buying used. Owners move a lot, or they have kids and need the space and they usually resell their bikes.
You can get a decent used bike for $100, quality is average. Those are bikes that sell new for around $250-$300. I have one of those as my city bike, a Raleigh mountain bike that I got off the Canadian Craigslist. It's a bike I can use to go to the market or downtown and not have to worry about it getting stolen. I use a cheap lightweight cable lock for it. I also use it to ride in winter over snowy/icy city roads as I don't have to worry about rust spots.
I have another bike, a Specialized Stumpjumper mountain bike from the early 00s which was worth about $1,000 new and the owner spent another $500+ in aftermarket parts (Mavic wheels and hub, hydraulic brake, clipless pedals etc), which I bought for $500 ten years ago. I use this bike only for trips in the country and trail riding.
I have a vintage Peugeot road bike that I use for commuting if the weather is nice, or for riding long city and country roads with my woman who is into that.
If you want just one bike for casual city and light trail riding, I would spend around $150-$250 for a good used bike, that is the sweet spot, where you can get a nice $500 bike with solid components (derailleur, shifter, brakes, wheels,...) that will require less maintenance and downtime and for which you won't have to spent $60 for a lock.
Don't bother with bikes with rear suspensions, get a hardtail. Rear suspensions are only good for serious trail and downhill riding, in city conditions the rear suspension sucks up some of your pedal power without much benefits, and cheaper bikes with rear suspension suck, you have to spend at least $750 to get a good one. Even a front shock might be superfluous for city riding.
For commuting, road bikes are great because they are faster, more efficient and narrower which helps cut through traffic. Hybrids are more comfortable though, especially if you're not too thin. I would wear a helmet with a road bike, because you're usually riding faster and with your back bent forward, so you would fly head first in a front collision. I wear a helmet when riding on serious mountain trails but don't bother wearing one when I'm riding on my casual mountain bike for local trips to the market or the park. Oh and if you don't live in California, I would get a bike with mudguards.
If I were you Hindy Man I would get either a used Bianchi Milano for $250-$350 hybrid bike, or a quality vintage road bike like that of WhiteWashed at just under that. The Milano is the coolest bike out there at this price range, exhudes classic Italian class, and very good quality, with an automatic 8-gear transmission:
