I have both an old laptop and an old desktop running debian linux. The laptop's ip is determined by dhcp and is usually 192.168.1.101 , and the desktop's ip is static at 192.168.1.170. Both have broadcast set to 192.168.1.255. Whenever I plug the laptop into the network, it can't resolve any hostnames or connect to anything, but when I take the desktop off the network, it works. This also occurs the other way around with the laptop blocking the desktop. What's going on here? Does it have to do with the ifconfig broadcast setting?

THIS is interesting.

It should not have to do anything with the broadcast, that is set fine.
1) I would do a lil power cycling of all devices. Your arp table might be foobar (Prob not, but it's possible) (ARP tables map mac addresses to ip's)

2) can you manually set IP's and check this?

3) What is serving dhcp and can you post dhcp settings?

Well, to tell the truth that laptop is the only box using DHCP. THe DHCP is server by a Linksys router. There aren't many settings, but...
Local DHCP server enabled
start ip address 192.168.1.100
number of addresses 50
dhcp address range 192.168.1.100 to 192.168.1.149
client lease time (0 minutes means one day) 0
dns 1 24.28.99.61
dns 2 24.28.99.62
dns 3 24.28.99.63
wins 0.0.1.1

This stays through power cycles but I'll try. Any order I should power cycle them in?

I don't have a philosphical reason for choosing so, but I would boot up the PC's first, then the router, etc.

Do you have a way to swap out routers or anything like that ? or perhaps wipe and reinstall the firmware to the linksys?

This is a crazy one, i must say ...

Well, I don't know that it has anything to do with this, but at one point I tried to put a hosting app on the desktop (I'll get the name for you), and the desktop has two ethernet adapters. I don't use one though. I'll try reseting the router and all. The settings on the router haven't been changed from defaults except to set up port forwarding, however, I use road runner and recently signed up for the rr with AOL bundle, in case that changes anything.

Also, when I do route on the laptop, it pops up with the dntry for 192.168.1.0 instantly, and then about 30 secs later comes up with default. Without the other box on, both come up instantly.

Why don't you do yourself a favor and put both boxes on dhcp then everything will work fine either that or turn off the dhcp in the router and use a static setting for both.

I set them both to dhcp and its working fine. No idea why it did that at all but thanks.