1) He's about 3 blocks away from me on his XTS2500 and we're on the same frequency, 462.6625. The deal is I can receive his transmission but he can't receive my transmission. I hear it might have something to do with the PL but then I saw somewhere that he can set a transmit freq and a receive freq. What's going on exactly. Is there a tutorial online somewhere that can show you how to set these up?
Also we should be able to transmit and receive on the same freq right? So long as one person is using the freq at the moment.

2) We want to program his radio using the Motorola CPS software. I have version R6.04.00 and we have a RIB-less cable. However when I try to read the device through both COM1 and COM2 I get errors. What's the deal with that? What's the current version of the Motorola CPS software? Do I need a RIB'ed cable and RIB?

You need to be using the same frequency, and either same PL/DPL squelch code or else carrier squelch.

The two most likely programming issues for your failure to communicate is either that one radio is set for a repeater offset (probably yours), so that it's transmitting on a different frequency than it's receiving, or else that one radio is set for carrier squelch (yours) and the other radio is set up for a squelch tone (his).

Well my MR350R is relatively simple. Is there anything I can do on my end to address those issues?

How do I navigate through the menus of his to disable the squelch tone?

Not familiar with the specifics of either of those radios, sorry.

You will probably need someone to "read" the radio programming on the XTS itself. Unless you know someone with the right Mot software, RIB (radio interface box) and cables/computer, you'll need to take it to a radio shop. It'll cost you $50 and up. At least a bench fee, whatever that might be.

I would hazard to guess that one of you is not transmitting on the same frequency you are listening. Like your radio might be setup to use a repeater.

ETA, I see you are using a bubble pack radio. I'm not sure those do "offsets" or not so I might indicate a squelch tone issue. For the $50 that radio costs you could have got a Saber.

Googled the model number and you're right, that's a bubble pack family radio service radio.  It's almost inconceivable that you have a repeater offset in your radio.  The radio does have "privacy codes", a somewhat deceptive terminology for tone squelch, so it's possible that is turned on.