If I've understood you correctly, the basic issue is this.
There's a noticable difference in pitch between the previously recorded Garage Band tracks & the new guitar track you're attempting to add.
Regardless how those previously recorded tracks were generated, they are what they are once you've recorded them onto the Tascam deck.
The challenge is getting additional tracks to match the existing pitch.
My advice ...trust your ears.
Since I don't know which instruments you're generating via Garageband, let me suggest this.
In addition your necessary Garageband tracks, record a sample tone on a separate track...something with a frequency range close to the guitar parts you'll be adding....a single guitar note, keyboard, whatever.
Purpose being to give yourself an easy point of comparison, something to help you match the pitch of the existing recording.
Tune your guitar as you always do, then before you begin recording, compare the pitch to your sample track & adjust accordingly.
Matching pitch on stringed instruments can be a real bi*ch ..too many variables!
Some of my songs contain 3 & 4 guitar tracks recorded at different times on different days.
And then you have overdubs.
Every new track I added, I went through a process similar to the one I suggested above.
Start by tuning to a digital tuner, then tweak it to make certain it was a good match to the tracks I'd already recorded.
Hope this helps a bit.