1st, I’m paranoid that people are watching me because to see a Clyde on a bike is not the norm here, at least I have never seen it.

Just get used to that, at least you're out riding, not sitting in a car or on a porch.

2nd, I’m not a fast rider, in fact I am anything but. I just like to take my time while others go at the speed of sound. And that makes me more paranoid because I keep thinking people are laughing at me going slower than them because I’m a Clyde.
I've seen lots of fast people, lots of slow people, i've ridden 8 miles an hour and passed people, I've ridden 20+ and been passed. Only ones laughing would be if they haven't done much riding, otherwise, they've seen it all, too.

3rd, I’m going through the learning process of getting the gears right for what I want to do. So when I come to an incline, I am sometimes not in the right gear and by the time I have figured it out its too late and I can’t pedal so have to get off.
I tried to avoid walking up hills, but never minded stopping to rest when I needed to. (You can pick up the rear wheel and let it spin while you downshift if you need to.)

4th, I’m not confident that a bike will hold up to my weight (310) and the last thing I want is to have to get off because of a broken something or other and have to push it home.
If you ride a bike long enough, you're going to break things or have malfunctions, weight or not. Usually, that means calling someone, not pushing it home, unless you're awfully close. But be prepared. Be prepared to fix flat tires when you're out, that's a more common issue that bikes collapsing under the weight.