As far as keeping track of what I have, while the collection was at home, all I had to do was look at the album. Now that it resides in a safe deposit box, the info is kept between my ears. I have a pretty good memory, reinforced by occasional visits to the bank. It's actually not too hard to remember most of it. For the type set, I know which six I don't have. (No points if you guess right.) For duplicates, it's gotten easier. Apart from the big six, I'm currently only missing five others for a second short set. Further multiples are a little trickier, and I sometimes find a note in the box that I forgot I had. Most of the interesting varieties I have, outside of the two type sets, I do remember.
I haven't always kept track of costs. Most of the more expensive ones I can remember, the common ones, not so much. I have been keeping track of more recent purchases, often because I got them at a good price, and consider them trade fodder, or sometimes material I can sell sub-retail for a small profit. I have been planning on going back and reconstructing records as much as possible, but haven't gotten around to it yet. I do have a small stack of old invoices scattered around.
As an old school collector, one who started before third party grading of currency, I have less faith in them than others. I've elsewhere expressed my views about their grading of uncirculated items. The middle grade stuff is a total mess. The standards seem to fluctuate with time. There are still a huge number of overgrades. Add to that, errors are common. I've seen a bunch of notes misidentified as to type, a bunch with misread handwritten serial numbers, and several misauthenticated notes. In fact, I've started to collect the last, adding a PMG graded T16 that's actually a counterfeit in just the last two weeks.
As for grading circulated notes, a debate once appeared on a (sadly, now defunct) Coins and Paper Money discussion board on eBay. I was strongly criticizing the TPGs. To make my point, I looked at some of the then current auctions, and by the third, I found a grossly overgraded note. I copied the scans of front and back, cropped off the label, and posted it to the thread, asking others to grade it. The responses included some stuff about people using different standards. So I went to the TPG's website and cut and pasted THEIR standards, requesting other board contributers to give their opinion based on the published criteria. The consensus was that the note in question was Very Good. I then posted the uncropped scans, showing the Very Fine label.
As to posting a collection to PMG's site, I'm only guessing, but they're probably only interested in things they have already graded. In general, I'd be leery about posting too many particulars about my collection anywhere on the Internet. With my opinions of TPGs in general, I'm not interested.