Do a search for ' photo workflow ' for some more tips on how to deal with photos ... There are lots of good articles, and lots of nice software options for organizing and sorting it on your computer....

you can (and should) do the baseline just with folders and filenames
pt1. hard drive of raw images.
folders of years and then within
folders of trips, special days or something denoting home images. prefixed with year month day (sorts better)
2010/1004xx_ecuador - april 2010, ecuador
2011/110910_caroline_and_tim - sept 10, 2012, caroline and tim (wedding)
2008/08q1xx_home - q1 2008, home
within these folders also year/month/day (for me roll) image number
2010/1004xx_ecuador/100402b_08.tif - april 2, 2010 second roll of the day, frame 8 (pad zeros!)
i suppose digitally it is
2010/1004xx_ecuador/100402_108.jpg - 108th image of the day.
pt2. making edits.
within the trip folder, make an image folder of the same name as the raw (w/o extension)
2010/1004xx_ecuador/100402_108
within that directory, year/month/day when the edit was made and reason of edit
2011/1104xx_armenia/110421q_03/1110xx_sildeluck
and then within that iterative steps on how the final is created.
2011/1104xx_armenia/110421q_03/1110xx_slideluck/00_basic_curves.psd
2011/1104xx_armenia/110421q_03/1110xx_sildeluck/01_edge_burn.psd
2011/1104xx_armenia/110421q_03/1110xx_sildeluck/02_spotted.psd
2011/1104xx_armenia/110421q_03/1110xx_sildeluck/03_bw_color_correct.psd
2011/1104xx_armenia/110421q_03/1110xx_sildeluck/04_submission_resize.psd
2011/1104xx_armenia/110421q_03/1110xx_sildeluck/05_unsharp_mask.psd
2011/1104xx_armenia/110421q_03/1110xx_sildeluck/06_as_jpeg.jpg
2011/1104xx_armenia/110421q_03/1110xx_sildeluck/final.jpg
this may be seem a waste of space... but space is cheap.
always keep 2 hd copies and every year, double the size of your hard drives and copy the entire old drive onto the new drive.
pt3. making galleries
i have a process that given a text file of folders/files, will generate unique folder. there's no real easy way to describe this.
a text file called 1101xx_slideluck.txt may look like:
2011/1104xx_armenia/110421c_10/1110xx_sildeluck/final.jpg
2011/1104xx_armenia/110422b_29/1110xx_sildeluck/final.jpg
2011/1104xx_armenia/110421p_01/1110xx_sildeluck/final.jpg
and makes corresponding folder directory
1101xx_slideluck/01.jpg
1101xx_slideluck/02.jpg
1101xx_slideluck/03.jpg
(there's also auto converting, resizing and enabling for web processes, but that just gets confusing)
the bigger details should be handled w/ metadata so an image can be tagged with
"***, dog, cemetery, blown out sky, 2008, oaxaca, mexico, cross"
Edited by: ewah
There's a suggestion and a half.
Or just use LightRoom or Aperture.
OP - give those 300 images a workout.

ManN, nice tips. Thanks. I'll give a try. I might have to delete some pics first. It's just too many...