A Digispark will never be unable to program itself - that is the premise of the Digispark and also a personal thing for me - I hate "development" boards that you need another board/programmer to use - to me then it is just a breakout board (which certainly have their place). I've also decided somewhere in this all that the Digispark will always be an Attiny device.
Will we ever produce an atmega device? - most certainly, but it will be its own line. Atmega328 devices have been done so many times, by so many talented people it just isn't a market we want to compete with right now - we couldn't make the extra core for less, and comparing their prices or our prices to China will never match up - heck we've yet to pay ourselves a dime and we still can't match Chinese prices, we never will be able to because even if we were to have it made there we still pay to get it to the US and pay taxes on it when it comes in and pay taxes on the income, don't have subsidized shipping, have much higher costs for utilities, buildings, etc. Someday we'll also have to pay people for providing support, community, instructions, etc - as my 9am-3am days are getting long. For this reason I do and will continue to ignore comparisons between our prices and Chinese prices. If someone ever says "Hey sparkfun/adafruit has this for less" that will have my attention, we carefully set our prices to be significantly more affordable than other quality US companies who provide similar levels of support, community, schematics, board files, instructions, etc.
When we make an atmega device it will be a breakout board or simple dev boardand it will be to compliment our flagship products like the DigiX and Digispark or it will be our own take on the standard Arduino aimed at lowering the price while still providing a US made, quality, and paying royalties to Arduino if requested. Which is another reason we've stayed away from the atmega arduino compatibles - we feel that innovation is just as important as affordability, etc - sure I can make an atmega board smaller, cheaper, etc - but in the end, at best, it will only be marginally better - the Digispark makes the attiny series far easier to use and inspires real innovation in using less resources, smaller boards, etc - we feel this is likely a reason for the interest it generates (it's not just another clone/derivative). If you're in need of an atmega based board I strongly recommend the extra core or femtoduino - they are both great boards made by great folks!