General heuristic: If you are not sure, if it is right to approach a stranger, just do it. Really. Talk to them next time.
And don't end your sentences with "lol", please.
And in general your heuristic is correct, but the gym is an odd place. I'm pretty social, but would prefer no one talk to me while working out. I'm usually so busy watching the clock and focusing on the task at hand that I don't want to seem rude to someone by having to eventually ignore them to finish my workout.
(I fear that all the image-substitution of smilies will create a generation of internet users that can't read the original ascii ones...)
As for the complements to a stranger, I did have a couple of random people at the gym say 'you've been working your ass off' or 'you've lost a lot of weight' in a non-creepy way when I was in line at the juice bar and I definitely appreciated it. But everyone's different.
When it comes to random complements it's really me projecting my anti-social tendency while at the gym. I'm there for one reason and it's to work out. I put headphones and generally don't talk or interact with anyone the entire time I'm there. I guess if the opportunity presents itself I'll try and offer a complement in a non-creep way :)
In lower middle class neighborhoods of Jersey City (JSQ), you can talk to others. Ask for a spot or advice on form, tell them "bad form, watch out", whatever. In Manhattan gyms (at least the 2 or 3 I've used), no one talks to anyone else. Ever.
My new gym is a big box gym. It's super nice, and I keep telling a friend of mine that really it's too nice. The people aren't very friendly, but I think that's because there are so many more people working out here that you rarely see the same person enough times to form any relationship. Plus, many people are there to just hang out and act like they are working out. One time I actually overheard a guy ask another guy for a spot and the guy told him no and then walked over to another bench and just sat down. I was stunned and in all my years of working out had never seen someone not help another when asked.
Even in their most competitive days I couldn't imagine Arnold telling Lou no if he needed a spot.
Working out really doesn't take that long. Most studies have shown that a typical non-steroid using weight training session only needs to last 45 minutes to an hour. After that time period, unless you consuming calories during the session the results you can get drop off dramatically from diminishing returns.
I agree that the biggest hurdle with people going to a gym is the intimidation factor. I'm in the gym 4 times/week and love seeing people who start and keep going. I want to tell them how awesome it is that they are doing it, but am never sure if that's the right thing to do some stranger lol.
If you can afford it the personal trainer is a great idea. The only problem is that many PTs plain out suck. I would try to do a session with one before committing to anything long term with a particular person. There are personality and knowledge factors that as a client you want to find out early.
Your story is also very common and is why a friend of mine is opening a gym that will cater to people who need a PT and are generally intimidated about the process. Obviously it will be a smaller niche gym, but I think it will work out pretty well.