Now for the questions after my life story.
1. Being a cigar smoker, is it best to get some heavy blends now (like GL Pease Odyssey/Abingdon) that I can really taste the flavors in? I am guessing that some of my problem is user error puffing entirely too fast to try to keep these bowls lit and actually experience some sort of flavor.
You can start off with some heavier blends, but what I would recommend would be to go at least a week without smoking anything. Allow your palate to get some rest. Then get a few different blends and go from there. FWIW I went from smoking 2-3 cigars a day to the pipe and I tried to rush the transition. Just grab a few blends that look good. There's a ton of pipe tobacco out there. We also have a newbie sampler trade for tobacco here http://www.cigarasylum.com/vb/showthread.php?t=9168 Also, when smoking start by smoking VERY slowly. A pipe is better served by having relights than puffing too hard. In time, you will get the hang of it...I still to this day do not light a bowl once and finish it without a relight. One trick I have learned is when lighting for the first time. Take a few puffs, then let it go out then tamp the ash down some and relight. This is often called a charring light. After that, I put the flame to my tobacco and puff away like a powerhouse a half dozen times or so to get the tobacco going. From that point on I puff slowly. Every so often I blow slowly back into the bowl to keep the ember going and try to not tamp too often while smoking...But like I said I still need relights while smoking. If the tobacco goes out I do not try to force it back. I just let it go out, put the pipe down and go grab a refill on my drink or whatever. Come back and relight.
2. I think I am going to order a MM Country Gentleman to try new tobaccos in until I find the right blends/styles that I like. Thoughts?
Go for it, I have a few cobs that still get smoked regularly. Great pipes, and great to learn how to smoke in.
3. What other brands would you recommend for someone who is used to a cigar type taste and not mildness for starting out to really get a feel for pipe flavors?
There are many blends with actual cigar leaf in them. Key Largo, Robustio, Dominican Maduro & Glory are a few that come to mind. I would start with getting a few straight blends. Get a blend that is just Virginia, One heavy with Latakia ( odyssey is good here ) and maybe a straight Burley blend to learn how the tobaccos taste as a stand alone smoke. From there when you go to smoke blended tobaccos it makes it easier, well it did for me, to identify the tobaccos in the blend. Also, it helped me learn and pick up on what the blender is trying to accomplish.