1) The Irman may be being swamped by the powerful output of the Pronto. You could play with using different distances.
2) There two software solutions I have found both use a 'remote' software programme on the remote control device which can be either a pc2000/2002 device or a windows PC. The pc to be controlled runs a server program which responds to messages sent from the 'remote' device via a network connection. The network connection can be hardwired/wifi or bluetooth. I'm using wifi because I already have a wifi access point into my home network.
You can buy ipaq's with bluetooth for about £200 on ebay or buy a cf adapter sleeve with built in bluetooth for around £50-70 and use your current ipaq. If you haven't got bluetooth on your pc you can buy a USB one for about £40.
If you are already familar with girder and creating Pronto ccfs I would use
netremote .
The ccf files have to be edited in Tonto but the install includes Tonto. Tonto is very similar to the Pronto software with useful extra features.
To control girder via netremote:
Edit your ccf and replace the ircode for each button with a special ircode '5001 0000 0000 0002 ffff 0000 0001 0000'. Then give the button name like 'DScaler.start'. Load the completed ccf into the 'remote' software and set the configuration details with the address of the pc to be controlled and a password.
Download the 'internet event server' plugin for girder and load into girder, use the settings option to set the password.
Create a command in Girder to complete required task. Click the learn button and press the matching button on your remote. Girder should recognise the message just like an ir learned command.
I haven't played with sending messages back to the remote yet.
If you want to control other equipment with IR codes then you will need a UIRT to send codes out from girder. I use a USB version which works with my Sky box and Rotel processor. The link from the remote is network only the ir output is not used.
One of the many advantages of this system is the cross platform compatibilty. If you want to use a small windows notebook or tablet pc to control the HTPC you don't have to start again with the control software. Also if your remote device supports it you can create larger ccf panels.
I hope this gives you the general idea. Let me know if you are still unsure about anything.