Programming with ethernet-serial-server

Has anyone else tried uploading sketch via an ethernet serial server? I'm using VSPE software by Eterlogic to map a virtual com port to a ethernet serial server which is connected to an Arduino clone. While the sketch is running, bidirectional serial data is successfully working. Is there a higher latency/response time then the usual method which causes the compiler to spit out the "no connection" error?

avrdude.exe: stk500_getsync(): not in sync: resp=0x0d

Does the compiler try to reconfigure the serial port when uploading? My goal here is to setup a remote debug/flashing setup via ethernet.

It's plausible, but my first suspicion would be that the remote serial port might not have the correct serial configuration. Do you know what serial settings your bootloader assumes? Does your remote serial accurately apply the same settings and control signals remotely that are applied to the local virtual COM port? I suppose it probably has to, but I wouldn't assume that until you've seen it work. For example I'd expect to see the Arduino reset due to the DTR signal change when the virtual COM port is opened - do you see that?

I was wondering what baud it used for programming. Looking at the boards.txt file I found, 57600 is what it's using. It doesn't seem to matter what baud I set when starting the virtual com port, the virtual com port uses whatever the windows program uses but the ethernet-serial-server needs the correct baud rate set manually. On this particular ethernet-serial-server, it does not look like it has a DTR line. At this time, I am planning to press the reset button until I get it working, then find a unit that supports the auto-reset.

So setting all baud rates to 57600 (including the Serial.begin function), it successfully programs the Arduino if I press the reset switch and the debug terminal then also works. Now I just need to figure out a clever hardware reset or find a ethernet serial server can supports it.

This got me thinking, I have a W5100 attached to this Arduino and the way my Arduino program monitors both the serial and the client object for data requests, I can access the Arduino's web server via the ethernet serial server the same as via the W5100. So my W5100 ethernet hardware become redundant. I just need an ethernet serial server shield instead of the ethernet shield + ethernet serial server...

If such a thing existed, it would be essentially an Arduino with an Ethernet port. There is a standard Arduino with an integral Ethernet port, and doubtless there are clones available too. The idea of using one Arduino as a bridge to program another is not novel and has been done several times, and I'm pretty sure you will find an implementation that uses Ethernet to upload the sketch if you look around. In case you're interested, there's also an Arduino clone with an integral wireless transceiver which can apparently be programmed via the wireless interface.