For code development, some kind of in-circuit programming is ideal. I dedicate a couple IO pins to programming with the MCUs I've been using. I use a programming header on the board for code development then remove it when I'm done.
My latest mod uses a two digit segment LED. The downside with those is you need 15 pins to control them (14 segments and a period). You can either use a shift register or a high pin count MCU to drive the display. I thought an LED display would be cool, but I'm not happy with it. You can't see the digits in direct sunlight and with only 2 of them, there's not much information you can display. The mod I'm currently working on will use a serial text mode display which has 32 characters, two lines with 16 per line. I'll be able to display a lot more information and driving it only requires 4 pins instead of 16. You can also use a serial graphic display if you want, but somewhat more involved to program. Check out the COG displays, they're highly compact.
Multiplex the two segments and you only need 9 pins, 10 with a period. Wire each segment in series and alternate the source. As long as it's faster than persistent vision it looks like they are both on.