check your firewall and your chilli.conf

it 's ok or not.

On uamallowed you can allow the ip or dpmain name your want to access with out authen. mrs.chilli allows all ports on the domain.
You don't need to allow the port.

or i understood your squestion?

Could I setup chillispot on a windows server and use it in conjunction with the wireless routers and current company internet connection?

A: There is no chillispot for Widnows Server. so you should install in linux server

Will chillispot allow me to create or modify the web interface taht uisers see so atht I can have my company logo and adverts up there?

A: You can do that but you must have programe system to manage it. such as php to create welcome page and company logo

You may find radius attribute but i never test it.

What i know about your need is
User 1 can always login all day but
User 2 can login only on the restricted time, such as the user can login only on 08.00 am - 11.00 am.

never seen about that.

I test only restrict how log to use not what time to login.

you can use proxy by set iptables rule.
dns server and set on chilli.conf

Errorrrrrrrrrrrrrrrrr

auth: user supplied User-Password does NOT match local User-Password
auth: Failed to validate the user.
  WARNING: Unprintable characters in the password. ?  Double-check the shared se                                                                             cret on the server and the NAS!
Delaying request 0 for 1 seconds
Finished request 0

Give me your chilli.conf and you authen pages and what is database you use?

You design to use freeradius.net and install on windows and use dd-wrt for chillispot.
I never use differrent  chilli and radius on local server.
maybe you can try install freeradius on windows config it.
And point dd-wrt to the windows ip. test it.
You may win man..

try https://help.ubuntu.com/community/WifiDocs/ChillispotHotspot/7.10

you may find new laptop to test ,it 's error on your laptop or on chilli. you will know .
and check on server chillispot is runing or not.

Regards

Or you may use lan to connect , if it got ip from chilli. it 's mean your inhel. (Oh No! it 's intel not inhel ;-D) your intel is not work.

Regards Again

How do you connect to your server from outside or inside?

this my config

EXTIF="eth0"
INTIF="eth1"

$IPTABLES -P INPUT DROP
$IPTABLES -P FORWARD ACCEPT
$IPTABLES -P OUTPUT ACCEPT

#Allow related and established on all interfaces (input)
$IPTABLES -A INPUT -m state --state RELATED,ESTABLISHED -j ACCEPT

#Allow releated, established and ssh on $EXTIF. Reject everything else.
$IPTABLES -A INPUT -i $EXTIF -p tcp -m tcp --dport 22 --syn -j ACCEPT
$IPTABLES -A INPUT -i $EXTIF -p tcp -m tcp --dport 80 --syn -j ACCEPT
$IPTABLES -A INPUT -i $EXTIF -j REJECT

#Allow related and established from $INTIF. Drop everything else.
$IPTABLES -A INPUT -i $INTIF -j DROP

#Allow http and https on other interfaces (input).
#This is only needed if authentication server is on same server as chilli
$IPTABLES -A INPUT -p tcp -m tcp --dport 80 --syn -j ACCEPT

some thing like this....

What you set for DHCP interfaces ?

WLAN , WAN

You should set on WLAN&LAN.

Did i understand your question?