Just thought I'd pop in here to post some positive results.
First off, went and got an evaluation at a local running store. The customer service, time they took with me, and their level of knowledge was outstanding. I wish I had a local cycling place like that...it would have saved me a good amount of pain having to learn on my own. Landed up with a pair of Saucony Guide 8 shoes...great fit, super comfortable.
Began my "training" yesterday and truth be told, I'm pleased with the results. For the moment I'm going to stick with the "complete not compete" plan and just get some time in. I ran 1.5 miles total with a .25 warm up, 1 mile run, .25 cool down. Didn't pay attention to time, did monitor HR. Did a nice pace on an indoor track and managed a solid run in the high 160's HR wise. Definitely not where I want to be...but better than before.
Cleaned up, went for a swim. Did my best to us what freestyle form I remember from over 20 years ago. Swam 7x 25yd laps in the pool. Again, baby steps.
The session left me feeling good...no real pain issues, the run went smooth...very positive about all of this.