It's not quite so easy with LW 5, though with LW 4 you could add descriptions to each file which others could see in their search results. This also helped files be found using special keywords in the description.
LW 5 does have this ability but not as advanced as LW 4 had, also they did not finish putting the description tool to either videos or programs. I find that annoying, since i cannot describe my vidoes.

Instead, what I do is find the file in the Shared List, right-click & selct View File Info..., then copy in the title plus a little extra information. This is what the people will see in their search result, though the filename will remain what it was originally.

For music, make sure you have reasonable id3 tags. I tag all mine as well as I can. This may include equivalent of description, album art, lyrics, etc.

For images I can give a description in the File Information description box. I use keywords I know people will use to search for a similar topic. Thus the hits on such files rises quite considerably.

As for browsing hosts. This has always been the hardest/most unreliable to do from the Upload window. Besides that, the Browse Host tool has never been 100% reliable. This may be due to the person being firewalled, or bandwidth or upload slots all full, or combination, etc. Many factors.

If I cannot browse them, I make a note of what they have just downloaded, then search for it. Wait a few minutes & Right click the search tab & choose Find More Results (need to wait 3-5 mins after a normal search because that's how long it can take for all results to return.) I repeat this cycle. Since people share their downloads by default, it means a reasonable chance that if they are sharing, then hopefully the searches will find a file they have downloaded from me. ie: I select all the results in the search results, then right click & choose Browse or ban host just to see who is listed as having those files. And compare to the person who was downloading from me to see if they are listed. This is also not a 100% guaranteed process but does give another option if you suspect they are not sharing & cannot browse them.