Example… I have a Ubuntu LAMP server that will need several IP address for the sake of hosting SSL sites. Can I assign more than 1 address with a DHCP reservation?
Not multiple per MAC but if you're VLAN tagging & trunking your NICs then your DHCP server will think they're different adapters.
In my home setup I'm using dnsmasq as a local dns and dhcp server. It has an option through which you can specify an IP address based on what it's called a "dhcp client identifier", i.e. a string which gets passed by the dhcp client to the dhcp server when requesting a lease.
I'm using it to assign the same ip to all of my laptops at home, either if they are on the wire or on the wifi connection (different MACs, same IP).
Hence, what I'm thinking of about your problem is you defining as many aliases of your NIC (eth0, eth0:1, eth0:2 ...) as needed and then having dhclient request a lease for each alias specifying every time a different client id (for example, "eth0", "eth0_1", "eth0_2" ...).
I'm not if this works and someone might well prove me wrong, but I'd give this a try: quick and easy to test.