Well the brake trick didn't last long for my truck and it's getting harder and harder to get it into gear. Eventually it's going to strand me so I gave in an let my mechanic take a look at it. At first they were wondering if it's the clutch but I was pretty sure it wasn't as the clutch had been replaced not too long ago, so I wasn't surprised at all to hear that yes indeed it's the transmission. They found a used one for me for $850 and out the door is going to be in the neighborhood of $1900. (Ouch).
Unfortunately that's going to impact the agility budget, but the truck is for the house so I may bill the house for part of it.
What's interesting is that it's cheaper to just replace the transmission rather than take it apart and find out why there are metal filings in the transmission fluid (I trust these folks as this would be a great way to rip someone off) I am having them keep the old transmission so I can take it apart to learn more about how it works.
Unfortunately the place they got the transmission from had a $200 refundable core charge which means they want the old one back or I give them another $200. Fun as pulling a transmission apart would be, it's not worth that much.
I did call them back as the clutch felt really soft and Rodell told me that the clutch was replaced (appartently you get a clutch out of the deal too as it's like trying to change the oil without changing the filter) and the new clutches are super smooth and they feel totally effortless (and hence wrong), but that it's normal and as long as it's going into gear that's ok.