Time to start going longer

So my plan for Justin involves getting him to run long off the bike. We can obviously only work on this on our weekend bricks so I want to keep our rides in th 80-90 km range but continue to lengthen the runs afterwards. Last week we did a 90km/10km brick and today's would be an 85km/11km combo. Remembering how he had to stop at the 7.5 km mark because of some dehydration I also wanted him to start dialing in his nutrition plan. So he fueled up with Heed and a PB sandwich and we were off. The wind wasn't significant but strong enough that we got a bit of a push heading north to Bloomington Rd and also east towards Uxbridge. Going through Goodwood I hit those same freaking railway tracks as the previous weekend and just like then I tossed a water bottle. Stop, turn around, pick up bottle, start to chase. This is getting repetitive. So off I went again chasing down Justin. I eventually caught up and as I did I noticed that he was slowing down. Apparently he'd just had a close call with a car making a left turn in front of him. It's times like those that I wish I could chase these dummies down and give then a good shaking. We hit our turnaround point and stopped for some quick nutrition and headed back ..... into the wind and bay did Justin's pace ever slow down. Hills and wind, his 2 nemeses. So we did 25 km into the wind along Bloomington before stopping for another break, turned north on Woodbine up to Aurora Sideroad before turning around and heading home. On the way home we dropped by Cyclepath to pick up chain degreaser to work on Justin's Dual after we'd done our brick. He's got it advertised and a couple of people interested in it and we were going to tune it and clean it up before anyone came to see it. We rode easy the rest of the way home and got changed for our run. It was hot out and I hadn't realized how much I'd been sweating until I saw the salt salty sweat stains on my shorts and jersey. I had a feeling I should have hydrated more. We headed out but unlike Thursday I didn't want to push Justin today. It was just about getting the distance in. We hit 5 km and Justin needed a break for a couple of minutes so we stopped at the traffic lights at McCowan before continuing for another half a km to turn around. We did another 2.5 km back to Markham Rd where Justin had to stop again. He was feeling rough and it was evident that he was dehydrated again just like last weekend. I wasn't feeling perfect myself and I don't think either one of us realized how much water we'd lost on the ride. After a few minutes we started running again but it only lasted about a km and Justin was cooked. We'd done 9 km and walked the last 2 km home. So at this point it's really important that we figure this out over the next few weeks. It will be hot and humid in Miami and we'll need to have our nutrition plan dialed in and working before then. I made him a chicken on a bagel and we sat down to "nutriate" albeit a bit late and then got out to work on the Dual. We spiffed it up and by the way he was looking at it I almost thought he wanted to keep it.