I'm the other Dave but I'll give you my responses to your questions, anyway.
1. Cross-connect them.
2. The Mini Socket iWiFi datasheet explicitly says to connect CTS/RTS if they are not used but says nothing about DTR/DSR so I don't think you need to connect them but you probably should ask this of Connect One Support.
3. I dropped my intent to make the shield work with 5V and 3.3V because it was just to complicated with all the SPI lines on the other modules. However, with the Mini Socket iWiFi, we are only dealing with two inputs and one output. The way I prefer to handle this is with a transistor and two resistors for each line. You can see example circuits in FIG 15 of AN213.
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