This is a badly messed up .htaccess file. Let's go over the problems...

In your first section, you say
  IF the domain is www.wayneglessner.com OR wayneglessner.com  AND
   the URI does NOT start with /wp/  AND
   it's NOT a legitimate FILE  AND
   it's NOT a legitimate DIRECTORY  THEN
insert /wp/ before whatever the user typed in.

This section is not firing for you. The "!-f" and "!-d" are normally used for dealing with 404 type errors, and shouldn't be mixed in with this section.

The next section checks for www.wayneglessner.com or wayneglessner.com, and tries to send an empty request (just the domain) to wp/index.php. This was not tested in your example. Once you get the previous section working, this one may become redundant.

The AddHandler and AddType rules should be moved out from within the URL rewriting code, just for cleanliness.

The next line seems to be at least part of your problem. For any image file, you're sending to directory "www.wayneglessner.com", which is probably not what was intended. What are you trying to do? Was this derived from some hotlink protection code?

Finally, in the Wordpress section (which appears to be hotlink protection for all files that contain a "."), you could cut the final 6 tests down to one. First of all, the last two will never fire because I don't think that the HTTP_REFERER is going to have the URI (wp/...). Isn't it just the referring domain? Anyway, you can condense them down to

RewriteCond %{HTTP_REFERER} !^$
RewriteCond %{HTTP_REFERER} !^http://(www\.)?wayneglessner\.com(/)?.*$      [NC]