I ride it a ton 1-3 miles, 100% grocery runs and similar 'around town errands'. A few trips further (12 miles round trip) on a dedicated bike/ped cross city trail (the burke-gillman in seattle). I'm still nervous on non-protected bike lanes/city streets. My commute too, if I ever go back to the office, is too long for this bike and the weight of it means I'm right at the edge of what the seattle metro bus bike rack weight limit is so no, first and last mile biking for my commute either.
That said it's a great little 'cargo-ish' neighborhood runner, I picked it mostly because there is a showroom in my neighborhood and talking to people who had them they seemed to like it. They have a similar step-through design that does not fold that I considered.
On the theft side, it's a concern, seattle like many cities has a problem with bicycle theft but so far my use-case means that i'm never far from the bike when it's locked up.
Of the ones on sale, you'll probably want either the RadRunner or the RadCity for the casual style, a good frame for cargo, and a huge rider height range so your friends and family can easily share it.
Outside a store or restaurant during business hours, however, is a much more risky proposition for a thief from all the foot traffic. They’d rather pursue low hanging fruit like apartment parking garages where their efforts will probably guarantee them a half dozen bikes in one go.
You should also always insure your bike. My renters insurance covers mine for theft with zero deductible.
Park it near other bikes. Lock it up properly with a good U-Lock (yes, these can be defeated but thieves are more likely to be opportunistic drug addicts than dorky guys with YouTube channels). Add a chain lock around the other tire if you’re super nervous. Don’t leave your bike outside overnight (locked up or not). Bring your bike into your home/apartment - even if your building has a bike room or bike parking area. Add your bike to your renter/homeowners insurance - this is not expensive and adds some peace of mind.
Yes, your bike might get stolen, but a lot of things might happen.
Video on the same topic: There's a proven way to stop bike theft. So why are so few cities doing it?
There’s a proven way to avoid putting innocent people to death by lethal injection (death penalty). There’s a proven way to eliminate the terror of medical bankruptcy. Why aren’t these things being done in America?
Edit: URL (sheesh) https://www.youtube.com/watch?v=RZkJP9D6fms
Ulock or chain the rest.
Everything you mentioned can be comfortably and easily done on like, a $300 single speed with a front basket. IMO just start there and see how well it meets your needs. Even if it fits them terribly, using it for a few months will give you a very clear idea of what you actually do need from a bike.