When I try your suggestion, I get:

$ sudo ifdown eth0.20
[sudo] password for alexeyt:
RTNETLINK answers: No such process
Internet Systems Consortium DHCP Client V3.1.3
Copyright 2004-2009 Internet Systems Consortium.
All rights reserved.
For info, please visit https://www.isc.org/software/dhcp/

Listening on LPF/eth0.20/00:1e:4f:b3:18:db
Sending on   LPF/eth0.20/00:1e:4f:b3:18:db
Sending on   Socket/fallback
DHCPRELEASE on eth0.20 to 10.10.20.1 port 67
send_packet: Network is unreachable
send_packet: please consult README file regarding broadcast address.
SIOCSIFFLAGS: Network is down
Removed VLAN -:eth0.20:-

$ sudo ifup eth0.20
Set name-type for VLAN subsystem. Should be visible in /proc/net/vlan/config
Added VLAN with VID == 20 to IF -:eth0:-
Internet Systems Consortium DHCP Client V3.1.3
Copyright 2004-2009 Internet Systems Consortium.
All rights reserved.
For info, please visit https://www.isc.org/software/dhcp/

SIOCSIFFLAGS: Network is down
SIOCSIFFLAGS: Network is down
Listening on LPF/eth0.20/00:1e:4f:b3:18:db
Sending on   LPF/eth0.20/00:1e:4f:b3:18:db
Sending on   Socket/fallback
DHCPDISCOVER on eth0.20 to 255.255.255.255 port 67 interval 3
send_packet: Network is down
receive_packet failed on eth0.20: Network is down
DHCPDISCOVER on eth0.20 to 255.255.255.255 port 67 interval 8
send_packet: Network is down
DHCPDISCOVER on eth0.20 to 255.255.255.255 port 67 interval 12
send_packet: Network is down
DHCPDISCOVER on eth0.20 to 255.255.255.255 port 67 interval 13
send_packet: Network is down
DHCPDISCOVER on eth0.20 to 255.255.255.255 port 67 interval 8
send_packet: Network is down
DHCPDISCOVER on eth0.20 to 255.255.255.255 port 67 interval 17
send_packet: Network is down
No DHCPOFFERS received.
No working leases in persistent database - sleeping.
RTNETLINK answers: Network is down
run-parts: /etc/network/if-up.d/avahi-autoipd exited with return code 2
ssh stop/waiting
ssh start/running, process 2076

I have 2 more data points: First, since I haven't removed any old
kernels since the problem began; I wanted to make sure that it's not a
kernel issue, so I rebooted with each of:

linux-image-2.6.35-23-generic
linux-image-2.6.35-24-generic
linux-image-2.6.35-25-generic
linux-image-2.6.35-27-generic
linux-image-2.6.35-28-generic

and I see the same symptoms under all of them.

Second, on one of the ~20 reboots since the problem started, the
interface came up OK and did not need to be started manually, so it
seems that the problem is intermittent.

Please let me know if I can do any more troubleshooting.

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https://bugs.launchpad.net/bugs/717243

Title:
  vlan interface won't start with ifup, can be started manually

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