Hello swstaff, thank you for your questions.
1. The simplest way to connect two pedals is using a serial chain, meaning you connect the output of one pedal directly to the input of the next pedal. In your setup, this means coming from the amp’s effect send to Input 1 of TF1, then taking TF1’s Output 1 and connecting it to TF2’s Input 1. Lastly, take TF2’s Output 1 and connect that to the amp’s effects return. Because you are running a mono signal, there is no need to use Output 2 on either pedal for anything.
Another option would be to connect the TimeFactors in parallel using an external mixer of some sort, something like an EHX Tri Parallel Mixer. The benefit here is you are able to not feed a delay directly into another delay, but rather mix both delays independently.
2. All factor series pedals including the TimeFactor can be updated and controlled using the H9 Control application. By connecting the TimeFactor via USB to a computer, users can see all available presets for every delay algorithm, and can create custom preset lists to download them into the pedal.
Here are a couple of brief videos explaining these concepts
Updating the Stompbox: https://youtu.be/SRSRCxaFBsA
Using H9 Control: https://youtu.be/V07NNTgxc_Y
How to create custom preset lists: https://youtu.be/Nfh00c2UhlU