RIPv2 – How to Exclude One Subnet

Best practice wise - should I let the router or the ASA handle NAT (Overloading)?

In the most general of design best practices NAT is performed between an inside and outside network. NAT overloading is generally performed at the edge when there is limited public IP address space. You can learn more about NAT overloading, also known as Port Address Translation or PAT, in RFC 2663 (PAT is referred to as Network Address Port Translation (NAPT) in section 4.1.2).

In this particular scenario you can argue that you have two inside and outside networks and will need to perform some form of NAT on both the ASA (whether that is the NAT overloading you're using now, NAT exemption, static NAT, etc) and the Cisco Router.

I can ping the 172.16.2.2 interface but not 172.16.2.1 from a pc connected to one of the layer 2 switches (proves intervlan routing is working -- i have a 172.20.100.8 address on the PC). Why can't I ping 172.16.2.1 from a PC but I can from the Layer 3 Switch?

The ASA 172.16.2.2 is receiving the ICMP echo-request but does not have a route back to 172.20.100.0/27. The echo-reply is actually being forwarded to the Router 172.16.1.1 via the default route.

And most of all -- Why can't I get out to the Internet from the Layer 3 switch?

Currently your ASA and Cisco Router do not have routes to internal devices other than their connected routes.

Your ASA configuration:

route outside 0.0.0.0 0.0.0.0 172.16.1.1 1

This will provide a default route via the outside interface, but how will the ASA know how to reach subnets residing behind the Layer 3 Distribution Switch?

You'll need to add routes to the internal subnets via the inside interface using the Layer 3 Distribution Switch as the next-hop IP address.

ASA static routing example:

route inside 172.19.12.0 255.255.255.240 172.16.2.2
route inside 172.19.3.0 255.255.255.0 172.16.2.2
route inside 172.20.100.0 255.255.255.224 172.16.2.2

Further reading: ASA static routing

Your Cisco Router's configuration:

ip route 0.0.0.0 0.0.0.0 200.200.200.200

Additionally, how will your border router know how to reach subnets other than it's connected routes, and the catch all default route via the outside interface's next-hop address 200.200.200.200?

Router static routing example:

ip route 172.19.12.0 255.255.255.240 172.16.1.10
ip route 172.19.3.0 255.255.255.0 172.16.1.10
ip route 172.19.100.0 255.255.255.224 172.16.1.10
ip route 172.16.2.0 255.255.255.224 172.16.1.10

Further reading: ISR static routing

I cannot get an ip address right now from the DHCP server (Windows). Any insight into why?

Ensure you have end-to-end IP reachability between the client(s) sending DHCP discover messages and the DHCP server.

From what I can gather from your topology and configuration, the subnets 172.19.3.0/24, 172.19.12.0/28 and 172.20.100.0/27 should have no issues connecting to each other (assuming they are configured to use their respective default gateways) from a networking perspective.

You can remove the ip helper-address syntax from the SVI 100 given that the DHCP server is on the same segment and that command is used for a DHCP server(s) that is on a different segment.

interface Vlan100
ip address 172.20.100.1 255.255.255.224
ip helper-address 172.20.100.27

RIPv2 with the no auto-summary option will advertise the specific routes, not the aggregated prefix, unless you you use the ip summary-address rip interface command.

The network statements in RIP are not specifically telling RIP what prefix(es) to advertise, they tell RIP which interfaces should participate in RIP, and RIP will get the specific prefix(es) from the interface(s) which fall into the network statement. This is true for most routing protocols on Cisco routers, and it is a source of confusion for many people. For instance:

interface FastEthernet0/0
 ip address 10.1.1.1 255.255.255.0

interface FastEthernet0/1
 ip address 10.2.2.1 255.255.255.0

interface FastEthernet1/0
 ip address 172.16.1.1 255.255.255.0

router rip
 version 2
 no auto-summary
 network 10.0.0.0

The above configuration will run RIP on F0/0 and F0/1, but not F1/0. RIP will advertise two routes: 10.1.1.0/24 and 10.2.2.0/24.

There are Cisco documents, such as Configuring Routing Information Protocol which explain RIP route summarization:

Restrictions to RIP Route Summarization

Supernet advertisement (advertising any network prefix less than its classful major network) is not allowed in RIP route summarization, other than advertising a supernet learned in the routing tables. Supernets learned on any interface that is subject to configuration are still learned. For example, the following summarization is invalid:

interface E1
.
.
.
ip summary-address rip 10.0.0.0 252.0.0.0 (invalid supernet summarization)

Each route summarization on an interface must have a unique major net, even if the subnet mask is unique. For example, the following is not permitted:

interface Ethernet1
.
.
.
ip summary-address rip 10.1.0.0 255.255.0.0
ip summary-address rip 10.2.0.0 255.255.0.0 (or different mask)