Transferring "large" file off of MS-DOS 5.0 Machine (without removing HDD)
Try using PKZip. It's an old DOS utility that provided some of the earliest zip file capability. You should be able to download it at http://wiki.oldos.org/Downloads/MSDOS. If the database is a text file, then PKZip should let you compress enough to get onto a floppy disk, or if not, then it should allow spanning of multiple disks. At that point, your main issue is getting from the floppy onto a more modern computer. I don't remember the syntax for PKZip, but I do remember that it does have very good help built in to show you exactly how to zip up and unzip files. I recommend version 2.04g from the downloads as that was universally regarded as the best version for many years.
Does the computer have QBasic installed? If so, you might be able to write a simple file splitter in it, something like this:
OPEN "database.dat" FOR BINARY AS #1
LET disk% = 1
LET todo& = LOF(1)
DO UNTIL todo& <= 0
PRINT "Insert disk"; disk%; "into drive A: and press enter.";
LINE INPUT ""; foo$
LET file$ = "A:\chunk" + LTRIM$(RTRIM$(STR$(disk%))) + ".dat"
OPEN file$ FOR BINARY AS #2
LET done& = 0
DO UNTIL done& >= 1300000 OR todo& <= 0
LET buf$ = SPACE$(4096)
IF todo& < LEN(buf$) THEN LET buf$ = SPACE$(todo&)
GET #1, , buf$
PUT #2, , buf$
LET done& = done& + LEN(buf$)
LET todo& = todo& - LEN(buf$)
LOOP
CLOSE #2
LET disk% = disk% + 1
BEEP
LOOP
CLOSE #1
This will split your database into chunks of 1.3 MB, which should fit comfortably on a 1.44 MB floppy even after accounting for FAT overhead.
Edit: Here's an updated version using binary I/O, which runs a lot faster, doesn't have issues with Ctrl-Z characters and correctly handles input files whose size is not a multiple of the buffer size. I've tested it under DOSBox, and it correctly split a 3 MB file of random bytes into chunks.
It's only 3 megs, so using a PKZIP with spanning would be the easiest solution, as others have said. However
If you had such a problem and the floppy drive did NOT work, using the serial port would be pretty easy.
To use a serial port, you need a DOS terminal program, and you would run it then use a protocol like ZMODEM, to transfer the file at 115kbps, which should take you less than 5 minutes at 115200 kbps.
On your laptop, or any other modern PC, you would need a USB-to-serial adaptor, and a null modem cable, and a terminal program that supports the same file transfer protocol. These cables should set you back about $5 each at most decent computer stores.
The best MS-DOS terminal program I ever used was called Telix version 3.12.
PKZIP does support spanning multiple floppies, and Lenovo has a DOS compatible app called CHOPPER that will also accomplish this.
http://support.lenovo.com/en_US/research/hints-or-tips/detail.page?LegacyDocID=DSHY-44QSCB
The pkzip switch for disk spanning (from docs):
-&[f|l|u Span disks [Format|format Low density|Unconditional format|
ul|w|v] Unconditional Low density|Wipe disk|enable dos Verify|
[s[drive]] Back up entire disk w/ subdirs (-rp) [drive to back up]]
Did the attorney explicitly specify that the database be provided in electronic format?
If not, and if this mission critical system has a functional (dot matrix) printer attached you could print the text file using the DOS print command.
For example:
print c:\file.txt /c /d:lpt1
Assuming printer speed of 100 lpm (~2.5 ppm) and 750 pages of text (estimated amount in 3Mb text file according to this calculator), then you should be able to produce a complete copy in about 5 hours.