How easy or difficult would it be to get a conditional release approved by the USAR to transfer to sister services or the Guard?

The grass isn't always greener on the other side. If the SM makes it into the IRR they are in a powerful position to then recon other units and situations if they want to be a TPU again.

I say this because I saw multiple soldiers of mine come from other services only try and get back to the BS and nonsense they left behind in their original service only to find themselves now locked into the USAR.

So, if they are simply trying to avoid a series of constant conflicts with the USAR given their current experience I caution them to be weary of where they plan to step next. My reasoning being that if a SM simply goes into a unit and situation blindly chances are they are going to be placed there by a retention or recruiting NCO that only sees the open positions in most dire situations needing to be filled. Chances are all those billets are going to suck regardless of MOS/Rank.

While in the IRR one can "ask around" before stepping back into a bad TPU situation. I personally look up the unit's UIC, and then pull the MTOE and METL information on the unit. Validate if it is RFX or TDA, and reach out to the unit and try and get a copy of the annual training schedule. I ask around if the unit has a full AGR complement and if the key positions of Commander, CSM, and 1SG are all filled.

*******
His best chance for matching up an ideal drilling status balance with civilian life is going to be back into TPU in the USAR. Going NG or another service starts the crap shoot all over again.

Our first enlistment or obligation of service is spent learning how to navigate the system. If we are lucky we survived it long enough to use the knowledge to our success going forward. Otherwise we just try and get to ETS and bail. Bouncing from one service/MOS to anther is more like playing the lottery than trying to work to get yourself a better hand.

Haven't tried to go the other way, but transferring from a Guard unit to the Army Reserve usually isn't much of an issue, particularly since this soldier has served the majority of her enlistment. Joining the Air Force as prior service seems to be problematic these days. They are the smallest service, excluding the Marines, and don't put much effort into recruiting outside of their own ranks. The Navy is better, especially if you have an MOS that can reasonably convert to a Rating.
I don't know how strict the Reserve side is about Conditional Releases these days. Guard units tended to deny them if the soldier hadn't served most of their enlistment in my day, although hardship was a valid reason to apply.

Are you close to ETS? Also, are you in a high density or low density MOS?
From my experience as a Army Reserve Administrator, those are two factors that could help with your transfer.

If you are close to your MOS, it could be better for you to reenlist or extend into the IRR and then go to the Guard or AC. Just don’t have a break in service.