- Can you request a health check from the Netduino?
- Can you extend the program memory size by using an SD card?
As for 2, there are a number of discussions on using the SD card as storage space for DLLs but keep in mind, once you load the DLL into memory, you're using the chip memory. You can't execute program space from the SD card directly. The SD card is primarily used to store log or resource files. I wouldn't count on being able to use this when decided on what boards to evaluate for your needs.
Side note: all consumer GPS receivers (sold in the US? made in the US? required by license?) have an arbitrary maximum operating altitude above which they will be unusable. Just something to be aware of when designing your project.