I will answer both questions.
Icon HDP is a much better DAC and headphone amp than Icon. Basically you want to reduce Icon to amp only for S-1.
Since HDP has optical in, you will get better performance with Airport Express.
Some people will buy Icon HDP just for the performance of the headphone amp alone. Some companies are selling a high performance 24bit/96Khz DAC and preamp for twice the price of HDP. Therefore when you look at it from cost or performance angle, it is worth introducing HDP into your system.
You can still migrate this system to higher performance when we introduce Icon Amp-100 in the future (at least 6 months away). In that case, you would have to buy the S-2

to match Icon HDP + Icon Amp-100. Then either sell or move the original Icon+S1+W1 to another room.