As this is your 'awakening' to dressing better, your best strategy is to, when your budget allows, replace each pair one by one. Now if you have the funds to go all out and replace the lot, that would be the best. However, if you can only upgrade one pair at a time, here is my list, based on your photos:
1, 2, 3 & 4 are all passable as Streetwear
5.These will need work by are salvageable. (See below *) Target these for termination when you get something better.
6. Abominations. Use them to take out the trash, burn them or throw them out.
7. You can wear Casual or Dress Casual, provided you maintain your suede. See below *
8. The deck shoes never go 'out of fashoin'. A summer shoe but in your case you can push it until first frost and only on rainy days. Strictly casual.
9. Florsheim Monks need to be cleaned up. Keep them until you can replace them. (See below *) Target these for termination when you get something better.
Suede: Buy from an Office Supply store, a few white erasers, you know, for students. Rub the eraser all over the suede to lift dirt.
Buy some Suede Protecter spray and a suede brush. After the eraser, use your suede brush in circles gently on the suede to raise the nap (fibres) Then spray lightly.
For all your other leather, some quick tips:
Buy Leather conditioner and some black polish (KIWI Creme polish Black)
For all the brown/natural leather, wipe with a clean damp terrycloth to remove as much dirt as possible.
Apply sparingly, leather lotion. Work in by hand. Let dry 15 min, brush w-clean brush, then buff with a clean cotton cloth.
For the black leather, same as for brown, but when dry, apply the KIWI polish sparingly with a finger. Let dry 15min. Brush, then buff.
Get yourself some Shoe Trees and use them. They will help restore and maintain the original shape of the shoes.
If you have none, use crumpled newspaper for now.
Finally....tell us more about yourself and your day to day lifestyle / activities and budget and we will help you select your next shoes.
Thank you for taking the time to post all the photos! It helped us help you 100%