Oly race speed = Long ride speed (Page 3)

He'll give you information that he thinks you need which will probably include some of both. Since it feels like you're being picked on from all angles, it might help to simplify who you're listening too. That is one guy you do want to pay attention to when he shows up. What he's asking can very well help in figuring out how to get more out of the training you put in and also why your speeds seem kind of flat for the effort put in.

I'm also curious about spending time in aero. Any idea how much and has it included harder efforts? 

Sounds to me like the "aggressive" tri fit on a road bike is part of the problem. I personally could not make the hybrid thing work, hip angle was too closed off and I couldn't create power while in the clip ons. 

But also if your previous post about zones is correct, you just aren't riding hard enough. 

I started riding with a group last year, they took me out, blew me up in the first 30 minutes and then dropped me like a bad habit. I had previously thought I was a good cyclists, not even close. I worked hard last year and finally got to where I could at least hold on for a ride. 

This year has been a compromise. I am in IM training so I try to keep my effort a bit lower than last year. I get dropped a bit on the hills this summer but I am able to catch back up. I have a riding buddy that is very close to the same riding ability as I am. He has been training hills and sprints this year so yes he can beat me up a hill and can take me on a sprint. However when he and I go for 100 mile rides he is out of gas long before I am. I was able to hold 18.2 mph average over 115 miles last weekend, I could have never thought of doing that 2 years ago. The intensity of the group ride has made me a much better cyclist overall. When you get accustomed to being put in the hurt locker on a regular basis, it makes your steady effort faster overall. When a hard effort is 25+mph, the holding 17-18 for a long time becomes much easier.

So my advice would be to either figure out some interval training. Or go get beat up by some cyclists that are much better than you. Best way to get better at any sport is to find someone better than you and try to keep up. 

Ok...so what am I missing here.

One ride you did at an avg HR of 162 and averaged 19.0 mph.  The other ride you did at an avg HR of 144 and averaged 17.6 mph.  You rode harder, you went faster.  Or were you expecting to go something like 21 mph given the additional 16 bpm on average.

If you are looking at the shorter ride, it seems like the first 28 minutes or so you are averaging 160ish HR but only going around 17-18 mph, but it also seems like you are going East into a headwind because as soon as you turn around and head back West, you're averaging between 21-25 mph at the same HR.

^^This is exactly what I was thinking.  I'm guessing a closed hip angle could be the smoking gun.

Two weeks may not be enough to make a huge difference, but I still suggest swimming more.  It looks like you clearly can go faster on shorter, hard riding days than long ones (didn't look at those files, but trust those that did and just noticed your 5k post where you said you were just under 17mph for a long ride and then 19+ for a short one a few days later).  So, aside from conditions and terrain, the only (physical) reason you would not be able to exceed your long ride pace in a shorter race is that the swim is taking more out of you than you think.  Certainly work on varying your riding intensities as Shane suggests (and spending more time at harder intensities if you are able), but to realize the full benefit of that work you need to get out of the water in good shape--so need to work on fitness there, too.