So I'll start at the beginning:

Drained the pan and got (~ 3 1/2 quarts) out. (Oof! especially after watching mtbtim's / timmythetoolman video), huge shout out to Tim and Sean. Those guys have made my life a lot easier prepping and doing work on my T4R.

Anyways, added the 3 1/2 quarts and proceeding to start flushing. Probably flushed somewhere in the realm of 10-12 quarts before I started getting clean fluid.

I think by now I've added an additional ~1 1/2 to 2 quarts (more than I started with) and I'm slightly below the cool line while having the engine hot. When checking the level I go through the gears first and then proceed to check. Note: my dipstick is oddly bent but will go in all the way.

Should i be concerned at all about my oddly bent dipstick throwing off my readings?

How far (quart) wise am I off from being full (being slightly below the cool line) when the engine is hot?

You say the engine is hot but is the transmission fluid at the right temp?
It should be about 158-176 degrees F.

I'd venture to guess if the engine is hot, why wouldn't the automatic transmission fluid be hot as well? There isn't any other way to tell that I'm aware of.

after pulling my dipstick in out and countless times I managed to break it. I guess I'm going to have to pull the pan if I can't get the dipstick tube loose. ugh.

You should be able to remove the diptstick tube, there is only one 12mm (I think its 12mm) bolt that holds it on. The tube can sometimes be a pain to separate from the bottom portion. Try a twisting motion to free it up, there is also an Oring between the two halves of the tube.

Just because the engine temp is at normal operating temperature, does not mean the transmission fluid is. For instance, it was -8 yesterday morning in Wisconsin. I let my truck fully warm up (185 deg ish) before I left for work. The transmission fluid was still reading below 80 degrees on my aftermarket gauge I have installed.

You need to drive around in town (lots of stopping and going) for a good 15 minutes (especially if its cold out) before it gets up to the normal operating temperature.

If you have a 99+ you can monitor it with a bluetooth obd2 reader with the torque app (scan gauge or ultra gauge works too). If not, you can use an infrared temp gun on the pan to get an approximate reading.

I drove around for about 10 mins before checking when it is "hot". The engine bay was hot enough to burn me so there's that as well. I also live in San Diego so I probably don't have to worry too much about the fluid temperature having trouble getting up to temperature.

Good to know on the dipstick tube. Hopefully I won't struggle too much with it and hopefully the rest of the tube is there.

Another way to check I use. If it's been sitting overnight on level ground cold is accurate. The A340F's are notorious for bending dipstick a certain way.
I filed a notch on handle so I put it in the same way everytime using reference point.

Great idea for the reference point. Correct me if I am wrong but cold still means when the engine is running right?

That's not going to get the trans hot. It is more like 20 minutes of around-town driving in the winter (SoCal winter, that is).

My ~20minute morning commute (17 miles, mostly freeway speeds with torque converter locked up) barely gets my trans fluid up to 140*F this time of year.

When you get a replacement dipstick, make sure you get the right part. The 2WD and 4WD are different, as are CA emissions vs. Fed emissions.

-Charlie

@APhelps , take heed to what @phattyduck said about specific dip stick been known to happen. Use the VIN.

Well I called camelback toyota and gave them my VIN so hopefully I'll get the right one.

I'll have to drive around for 30 minutes then and go from there.

I sorta just figured if the engine is hot enough to burn me than the tranmission fluid is going to be warm enough to be checked, given there isn't any other way to check the temperature.

Good information though.

I don't start it, if it is setting on level ground all night.

NO!!, you keep missing the point here.
Engine gets hot from internal cumbustion, Trans fluid gets hot from running fluid through radiator trans cooler/warmer.
Trans fluid expands over time as it flows once it reaches 180*F for a while.
Trans is forgiving on hi/lo level and problems, it's 57* here I would do 70 mph
on insterstate for 20 mi plus 6mi @ 45 mph getting to n from I55.
Your good since D&F was 3.5 qt, mine is 3.5-4 qt depending where I want it on stick.

Quick and simple... Start the engine and set parking brake. Step on brake pedal with left foot and put it in drive. Leave foot on brake pedal with good pressure and rev engine to about 1400 rpm. This will heat up the trans to 180 in less than 4 minutes. Put back in park and leave engine running. Check fluid level.

I've used this method every time I've done a drain and fill, and use my reader and torque app to get the transmission temp.

I understand the principles of the differences between the engine and transmission. (hopefully i'm not coming off as ungrateful here) If the engine is hot enough the coolant is certainly going to be hot enough as well to exchange the heat from the coolant to the transmission fluid. How long is hot enough though, apparently I didn't get it hot enough.

I'm not sure the transmission is as forgiving on the low side of fluid since you'll run hotter faster with less fluid over the long term.

It does appear that I wasn't getting it hot enough so I'll have to drive it on the freeway and see what happens.

I've definitely put more than 4 qts in my transmission since the D&F so I'm a bit leery of the level now. I'm sure when I was flushing things out I put a little less than a quart in for every quart (or so) that came out. Even with the transmission cold and running I still wasn't hitting the correct marks on the dipstick with solid fluid. My fluid is on the dipstick so I'm not overly concerned but I'm not quite there (or was for that matter).