The bike I finally settled on was a 2014 Specialized Hardrock Sport Disc 29er from Gray Goat Sports.
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The first pair I tried felt OK-- until I tried on the second pair. That's when I realized exactly what the salesman was talking about. 
UPDATE
At the recommendation of several folks to invest in a quality pair of biking shorts, I set out in my typical style of research-then-purchase.
I first turned my nose up at the idea because I wasn't interested in hitting the trails in spandex. But I quickly learned that "baggies" are cargo-style shorts with built-in (sometimes removable) liners with the padded chamois found in all biking shorts. An alternative and more versatile option is to purchase and wear road bike shorts underneath loose fitting athletic shorts or board shorts. I decided on the latter because it saves me from buying several pairs of $100 dedicated MTB shorts.
I went back to Gray Goat Sports to see what they had to offer. As has been typical, they started by asking questions about my riding style and then educating me on the current industry standards. I was given 5 different shorts to try, from 3 different manufacturers, priced from $35 to $60. They explained that biking shorts fit every person a little differently, so trying them on is the best way to go. And I'm glad I did, because I would've had zero frame of reference for how shorts with padded crotches are supposed to feel.
I sampled them without looking at price tags as to not bias myself. The pair I chose were $55, the second-to-highest priced pair. The first pair I had tried on that felt like a diaper ended up being the least expensive at $35. So glad I didn't buy online. I got 10% off because I bought a bike from them this year. So $50 + tax. I looked them up online when I got home and found most online retailers were selling them for $55-60.
For those who have never used a pair of biking shorts, that's the chamois pad that I'm talking about. (the shorts are inside-out) I can't quite figure out what it resembles more-- Goofy or an evil Jar Jar Binks.
I then went over to TJ Maxx and picked up a couple pairs of lightweight board shorts for under $20 a pair. Wearing them in conjunction with the bike shorts makes for an effective and reasonably priced combo that gives me the functionality and style I was looking for.
While at TJ Maxx I also came across a cheapie no-name hydration pack. It was the perfect size (small) for carrying the basic essentials and my phone and keys while I'm out on the trail. I paid $16 for it, removed the bladder, and added some paracord zipper pulls.
Eager to try out the new gear I decided to wake up early the next morning and go for a ride. I was on the trail at Southwestway Park by 8am. This was my first solo ride, so I was sure to be cautious. Which I am anyway because I'm still fairly inexperienced. I used the mountain bike version of the Runtastic mobile app to track my ride, which was very cool. Ride duration was 49 minutes and I rode 4.13 miles.
I did experience a personal victory. At SWW there is one climb that is somewhat steep, and very long. In the past I've made it up the first 1/3 and then pushed the bike up the remaining portion. The reward for all the huffing and puffing is that at the top you can chose from 2 downhill flow tracks that are like roller coasters on bikes. In the past I've tried this climb early in the session. After doing some reading about appropriate use of the 'granny gear' and proper pedal cadence, along with attempting it later in the session, I was able to climb the entire hill without stopping! Here's an upshot just before I made the climb. You can only see the first half because the second half continues up into the woods.
The new shorts worked great. They were comfortable and allowed me to focus on the trail and not my sore bum or chafing thighs. The new pack also impressed me. It was small enough and light enough and stayed in place such that I didn't notice it at all. Time will tell on how long it holds up, as the materials aren't heavy duty.
My confidence level is increasing with every ride. I'm thinking less about shifting gears, so I can now focus on other aspects like weight distribution and braking. Going solo was interesting in that I could go at my own pace and not feel like I had to keep up with the pack. I had time to enjoy my surroundings and take in the outdoors air. At one point I watched a fox trot across a clearing. I was coming off a very busy and stressful week at work, so I really enjoyed the peace and quiet time.
Next thing I'm needing is a 3- or 4-bike rack that connects to a 2" hitch. I see them come up on Craigslist from time-to-time but they go fairly quickly.
That's all for now-- will update as things progress.
