You've gotten great advice here -- any plan followed will lead to satisfaction, if you supply the perseverance.

Speaking only for myself, and knowing my inclinations are not everyone's, I would go for the 5/8 or 6/8 Dovo Best package from SRT and save $40 (put the money away in a safe place; if you're like most of us, you'll soon be sending it right along to Lynn and Don), and specify a 3" strop for a couple extra dollars. Stropping is critical, and one of the more difficult skills to master (and one of the most catastrophic if not mastered). Being able to run the full length of the blade is one variable taken out of the equation. If you find you enjoy this sport, you'll probably want a second razor soon, and can spend the balance of your budget on a Bismarck. If you really enjoy shaving with a straight, can't get enough of it, want to spend all your free time in the shave den, etc., you will certainly get interested in honing, and then your $300 startup will be akin to purchasing the front porch of a house -- then wanting to add three bedrooms, a couple of baths, living room, etc. There is no end until your banker drops you a line....