Some Content On Site Will Not Index

I have a site up and running, cron is working, all the basics are in place- and it will not index to 100%! I've reindexed the site twice now, and it consistently comes up with 5 items left to index, which will not index no matter how many times I run cron. They seem to be in the first 100 nodes though, as clearing the search index says I have 248 nodes. After a cron run of 100 nodes, It says I have 153 left to index.

This one is totally beyond me, I have no idea why this isn't working. The client is in a tizzy because of this though.

On a different, but related note, the index doesn't seem to be working very well. I've replaced the default Search box and results with a views+exposed filter based solution, but it gets the same results as the default search. Basically, the whole thing is extremely picky- I have an article called "WRAP extends enviro wine program to U.S.". A search for "wrap" find that article and a number of others, but a search for "wrap extends" finds nothing. This is a pretty new node, so I don't think it's one of the five; plus this is only one example. I have the Porter-Stemmer module installed as well, no help there.