I would say you want to test what happens with the break.
I have done triathlons Swim-Bike-Run all relatively OK
I have done duathlons - Run-Bike-Run Horrific cramp infested changeovers on both transitions.
Why the difference I don't know but running before a bike kills my calves.
Equally you need to work out what happens if you run 26 miles then stop for 30-minutes or 1-hour or 1-30 and then go again. You don't need a long second run, just need to see what happens on the first few miles. So you could try 13-miles then home rested, fuelled and out the door again 1-hour later. Get the body used to this unnecessary abuse.
Biking generally has a good cross over to running. I use FIRST for all marathons I have trained for. But would also suggest ou build in some double training runs e.g. Sunday evening Monday morning (if you need Saturday for family commitments)
A 3:26 single to an 8-hour double seems a tough leap. How are you going to achieve the improvements? Weightloss (would help me), improved fitness, more scientific training? Although if you have been using first sounds like you haven't been just doing the run till drop plan.
Logistics at the break for food and warmth will also be important. Getting cold could cause issues.
Hope this helps