Your choice of development platform is going to be heavily restricted by the tools available. For the more niche uControllers, you might find there is little choice. One thing is for sure, none of the tool vendors are going to be remotely interested in supported Chromebooks as a distinct platform as it's a minuscule proportion of an already small market. Likewise, web-service based tools are also highly niche, and I'm hard pressed to understand why anybody would want them.
Your best bet is to install Linux - provided the development tools you want to use run under it. GCC certainly can, but for proprietary tools it's likely to have to be some flavour of Windows - and most likely XP.
The lack of serial port is easily overcome with a USB-Serial dongle. Avoid dongles built on the PL2303 chipset where the unholy trinity of buggy drivers, silicon and possibly even devices is common. Devices built on the FTDI chipset seem much more reliable, but are more expensive. Using TRRS as a serial port sound like a nightmare: remember the console interface is the way you're going to debug your system - you need to trust that it works reliably.