Classic Printing Wierdness

Hi all,
I am encountering several very strange problems when I try to print from Classic. I'll be as detailed as I can, so bear with me.
1. Chosen printers do not stay chosen from one Classic restart to the next. Whenever I restart classic, there is no printer chosen by default.
2. The problem stated in #1 above only affects some Classic apps. I can start classic and run Claris Draw (for example) without ever choosing a printer and when I try to print something, I see an OS 9 dialog that includes a printer pick list and both of my printers are listed in it even if they are not listed in the Chooser (and one of the two is definitely NOT listed in the Chooser). If I select one from Claris Draw and print, it seems to take a few seconds longer than printing from OS X, but it prints just fine.
3. On the other hand, if I try printing without ever touching the Chooser from another app, namely Managing Your Money 7.2 (by the way, both Claris Draw and MYM are vintage 1997 apps), I get an error message saying "This printer cannot print because this application is not Apple Event aware and you have not installed Desktop Print 2.0 software." I don't even remember what Desktop Print 2.0 software is. But I know I have a boatload of extensions in my "Extensions Disabled" folder in my Classic system folder. If it is in there and I can reenable it, I hope someone can tell me how. But I really think this error message is not getting at the root of the problem.
4. For one of my printers, an HP OfficeJet 7310 All in One, I have OS 9 drivers in the Classic system folder. I have a printer option that shows up in the Chooser called "hp aio print". If I open Classic and then choose this printer before printing, Claris Draw still prints fine, although the print dialog that I get is now specific to the OfficeJet 7310 and has far fewer options. When I try to print from MYM after choosing "hp aio print", I get the exact same print dialog as in Claris Draw, but when I say OK, I see the job spooling and then an error dialog from the OS 9 Print Spooler is shown saying something like "Not enough memory to print this document. Try closing other applications and printing again." Of course, at this point, MYM is the only Classic app I have open and as I said, I only have the bare essential Classic extensions. Furthermore, in Classic, the Memory control panel is not supported, so it's not like I can go and allocate more memory to the Print Spooler.
So is this a real shortcoming of MYM or is it a Classic configuration problem? When I was able to run MYM under native OS 9, I printed all the time. To be honest, I don't recall if I have ever printed from it under Classic and I doubt that I have since getting my HP printer or my iMac G5. But one thing is certain, I can't print from it now under Classic.
I have emailed HP about this and am still waiting for an answer, but any advice would be greatly appreciated.
By the way, I already know that I can print to a PDF or postscript file and then open it in OS X and print it from there. In fact, that is what I have been doing as a workaround since discovering this problem.
Sincere thanks ahead of time,
Bill
iMac G5 20 inch, 1.5 MB RAM Mac OS X (10.4.8) Classic 9.2.2

Thanks B3av1s. I bumped the memory requirements for Print Monitor, MYM, and Chooser all by a factor of 10 (which is easy to do these days without evening putting a dent in your available RAM). I initially had similar troubles (without the memory errors) but I just now tried again since I had more time and to my surprise, I was able to print a 13-page job from MYM without error.
Otherwise, all of the other weirdness (by the way, please forgive the misspelling of weirdness in the title) is still there. Printers Chosen do not stay Chosen and if I do not explicitly Choose the "hp aio print" printer each time I start Classic, I get all of the errors I described before.
But at least this partially solved the problem.
Has anyone run into this sort of thing before? Is there a bug in printer support in Classic? Or in Apple's Classic implementation of the Chooser? If so, this is one I would love to see fixed.
Thanks again. If anyone has anything to add, it would be much appreciated. I'm going to mark this as question answered since I was at least able to print something. But I still think there is a significant mystery here that I would like to solve.

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I have used an Epson SP785EX on my iMac G5 under OSX
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expecially when printing from Classic.
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After having
tried everything including resetting the printing
system it is still not clear what exactly causes the
loss of the USB Port.
Classic does not have direct access to hardware, including USB ports.
However it may have to do with
restarting or switching users. When in the chooser
after selecting the original Epson Printer driver
(which I have reinstalled many times) the Port (USB
1) does not show in the 'choose printer port list'
(nothing at all shows).
This is normal.
I have also tried the
'LaserWriter 8' solution which I do not understand.
Just print, normally. The LW8 dialog box will pop up. You can then select the printer you want to use. (I have several printers on my system, two HP inkjets, a Brother laser, a label printer, a fax modem, and Adobe PDF)
1 type cmd-p or however you normally print
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Perhaps someone can explain or point me to some
literature. LaserWriter 8 shows in the Chooser but
again nothing shows on the right pane of the Window.
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apprecated.
Just print. That's all.
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I know it is possible because I have two Macs connected to the same printer, and it works on one and not the other. I can't figure out why.
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OK, I have finally solved the problem -- mostly.
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I want to keep my OS 9
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this worth the possible troubles?
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New printers are
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