S2S VPN - ASA 5505 to ASA 5540 - Routing Problems

Question

I'm a software developer (no doubt the issue) trying to setup my remote office (5505) to the main office (5540). No problem getting the S2S VPN up, but I definitely have problems with the routing. Using tracert, it shows it going into the remote network for a couple of hops, but then timing out. Packet tracer shows everything is fine. Using my client VPN credentials to the remote network, same on the return path...does a few hops, then gets lost. I've stripped down the config to the basics and ensured it isn't security settings on both ends, but still doesn't work. I've spent A LOT of hours trying to get this to work, so thanks for any assistance!
Current running config:
ASA Version 8.2(5)
hostname asa15
enable password XXXXX encrypted
passwd XXXXX encrypted
names
name 10.0.0.0 remote-network
interface Ethernet0/0
switchport access vlan 2
interface Ethernet0/1
interface Ethernet0/2
interface Ethernet0/3
interface Ethernet0/4
interface Ethernet0/5
interface Ethernet0/6
interface Ethernet0/7
interface Vlan1
nameif inside
security-level 100
ip address 172.16.5.1 255.255.255.0
interface Vlan2
nameif outside
security-level 0
ip address dhcp setroute
ftp mode passive
access-list outside_1_cryptomap extended permit ip 172.16.5.0 255.255.255.0 remote-network 255.0.0.0
access-list inside_nat0_outbound extended permit ip 172.16.5.0 255.255.255.0 remote-network 255.0.0.0
access-list inside_access_in extended permit ip 172.16.5.0 255.255.255.0 remote-network 255.0.0.0
access-list inside_nat0_outbound_1 extended permit ip 172.16.5.0 255.255.255.0 remote-network 255.0.0.0
pager lines 24
logging enable
logging asdm informational
mtu outside 1500
mtu inside 1500
icmp unreachable rate-limit 1 burst-size 1
asdm location remote-network 255.0.0.0 inside
no asdm history enable
arp timeout 14400
global (outside) 1 interface
nat (inside) 0 access-list inside_nat0_outbound_1
nat (inside) 1 0.0.0.0 0.0.0.0
access-group inside_access_in in interface inside
route outside 0.0.0.0 0.0.0.0 99.X.X.7 1
timeout xlate 3:00:00
timeout conn 1:00:00 half-closed 0:10:00 udp 0:02:00 icmp 0:00:02
timeout sunrpc 0:10:00 h323 0:05:00 h225 1:00:00 mgcp 0:05:00 mgcp-pat 0:05:00
timeout sip 0:30:00 sip_media 0:02:00 sip-invite 0:03:00 sip-disconnect 0:02:00
timeout sip-provisional-media 0:02:00 uauth 0:05:00 absolute
timeout tcp-proxy-reassembly 0:01:00
timeout floating-conn 0:00:00
dynamic-access-policy-record DfltAccessPolicy
http server enable
http 172.16.5.0 255.255.255.0 inside
no snmp-server location
no snmp-server contact
snmp-server enable traps snmp authentication linkup linkdown coldstart
crypto ipsec transform-set ESP-AES-128-SHA esp-aes esp-sha-hmac
crypto ipsec transform-set ESP-AES-128-MD5 esp-aes esp-md5-hmac
crypto ipsec transform-set ESP-AES-192-SHA esp-aes-192 esp-sha-hmac
crypto ipsec transform-set ESP-AES-192-MD5 esp-aes-192 esp-md5-hmac
crypto ipsec transform-set ESP-AES-256-SHA esp-aes-256 esp-sha-hmac
crypto ipsec transform-set ESP-AES-256-MD5 esp-aes-256 esp-md5-hmac
crypto ipsec transform-set ESP-3DES-SHA esp-3des esp-sha-hmac
crypto ipsec transform-set ESP-3DES-MD5 esp-3des esp-md5-hmac
crypto ipsec transform-set ESP-DES-SHA esp-des esp-sha-hmac
crypto ipsec transform-set ESP-DES-MD5 esp-des esp-md5-hmac
crypto ipsec security-association lifetime seconds 3600
crypto ipsec security-association lifetime kilobytes 4608000
crypto map outside_map 1 match address outside_1_cryptomap
crypto map outside_map 1 set peer 99.X.X.7
crypto map outside_map 1 set transform-set ESP-AES-128-SHA
crypto map outside_map 1 set reverse-route
crypto map outside_map interface outside
crypto isakmp enable outside
crypto isakmp policy 10
authentication pre-share
encryption aes
hash sha
group 2
lifetime 28800
vpn-addr-assign local reuse-delay 5
telnet timeout 5
ssh timeout 5
console timeout 0
dhcpd auto_config outside
dhcpd address 172.16.5.100-172.16.5.130 inside
dhcpd auto_config outside interface inside
dhcpd enable inside
threat-detection basic-threat
threat-detection statistics access-list
threat-detection statistics tcp-intercept rate-interval 30 burst-rate 400 average-rate 200
webvpn
tunnel-group 99.X.X.7 type ipsec-l2l
tunnel-group 99.X.X.7 ipsec-attributes
pre-shared-key XXXXX
class-map inspection_default
match default-inspection-traffic
policy-map type inspect dns preset_dns_map
parameters
message-length maximum client auto
message-length maximum 512
policy-map global_policy
class inspection_default
inspect dns preset_dns_map
inspect ftp
inspect h323 h225
inspect h323 ras
inspect rsh
inspect rtsp
inspect esmtp
inspect sqlnet
inspect skinny
inspect sunrpc
inspect xdmcp
inspect sip
inspect netbios
inspect tftp
inspect ip-options
service-policy global_policy global
prompt hostname context
no call-home reporting anonymous
: end

Answer 1

just out of curiosity, why do you have
route outside 0.0.0.0 0.0.0.0 99.X.X.7 1
You already set your default route through DHCP setroute under the interface. this could be the issue.
If your VPN config is ok and you are seeing encaps/decaps, it is likely a routing issue.
Does the remote device have the correct default gateway?
May be a Natting issue if you have a one-way tunnel (usually send but no receive)...
Patrick