So I started this get in shape crap at 278 lbs (I know, how did I ever let myself get that way?).  I'm currently around 256.  When I got back from Lake Powell, I was really excited because I was actually around 254 but apparently I was just dehydrated because I gained a couple of lbs back after I drank a bunch of water.  So I've still got a ways to go but I'm happy with the results. Although I'm getting a little bit back into shape, I'm still very out of shape.  I realized this when everyone was hopping in and out of boats whereas I had to kind of crawl on and off so I wouldn't lose my balance.  Even the 65 year old guy was getting around better than I was.  Basically I have become the old guy that everyone has to help out with.
One of the most frustrating things is that I don't think I'm really getting much stronger because I'm still not able to do much of the heavy lifting.  I remember how well I did when I was doing Crossfit full time even though I wasn't really eating that great.  Now I'm eating good but not exercising great.  Hopefully one day I will be able to do both so I can truly measure what my results would be. 
In our WOD yesterday we did crap load of pull-ups and push presses (It was supposed to be hand stand push ups instead of push presses, but I don't quite trust my back or my equilibrium at this time).  Today I can definitely feeling some pain in my shoulders.  But that is an awesome feeling because I know it's pain from working out and building muscle, not just the pain from my spine grinding.  So it's the proverbial "Good Kinda Pain".