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Rav Moshe Eisemann wrote a book about Dovid HaMelech called "Music Made in Heaven" - the subtitle of the book is "some thoughts on Dovid Hamelech and Sefer Tehillim." He does not go systematically through Tehillim, but he uses Tehillim as a means of analyzing events in Dovid Hamelech's life. I think it could largely satisfy what you are looking for. It's ...
JPS is publishing an English edition. I asked about its contents here; it's a condensed version, but at one volume per book of torah it covers a lot more ground than a one-volume chumash. I'm very happy with the volume I've used and plan to add the rest to my library. Sh'mot, Vayikra, and B'midbar have been released; D'varim is due in April 2015, and I ...
Judaica Press publishes a set of Mikraos Gedolos with a digest of the commentaries in English.
Try Wikisource - he.wikisource.org - צוואת רבי יהודה החסיד. Can't vouch for its completeness, but it seems to be there. Hat tip: Google.
If you're interested in buying meforshim individually (in which case they will come with many more editorial and elucidation notes), here's a few: Artscroll Rashi Artscroll Ramban Artscroll Seforno Artscroll Baal HaTurim Menucha Publishers Kli Yakar on Bereishis and Shemos Urim Ohr HaChaim I didn't shop around for which websites would be the cheapest, ...
You can download R. Yitzchak Berkowitz’s shiurim on Chelek Gimmel of the Mishnah Berurah from here
Rabbi Nissan Kaplan has a good set of shiurim he also goes through most of chelek 3 in the mishna berura here
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