Yes, the 2720H was a real bow-wow, and I'm shying away from ICOM VHF as a result. If, however, you live in range of a DSTAR repeater, you may want to consider it. There's a lot of DSTAR activity in the Chicago area, so you might well be in range.
I haven't played with the FT-8800 or 8900, but we have an FT-7800 in the family, and it's a very nice rig to use - simple and elegant.
The TM-V71's EchoLink interface is a very good one. Most EchoLink installations rely on VOX operation to start the sending of received audio over the Internet. The Kenwood interface uses the actual received carrier detection - a much cleaner setup. I have the TM-D710, and I really like it. If you're going to do APRS, you could upgrade the TM-V71 to have the functions of the 710 later with the addition of the RC-D710 control head, but it would be much cheaper to get the 710 from the start.
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