Edge condition issue?

I suppose this belongs in the Honing section?

I have two straights in my rotation. I have a vintage Morley Clover left to me by my great grandfather (more info here: http://straightrazorpalace.com/razor...ey-clover.html). Then I bought a nice Blue Steel with real ivory scales from a user here. I used them for a couple months about once per week. They dulled up pretty quickly. They pulled badly when shaving, and it makes a tear come to my eye. I haven't used them in many months as a result. I'm not real sure if it's my stropping techniques or the result of the original honing, or if this is typical. Before every shave, I was stropping on the leather a good 40x before each shave. Eventually, I got some diamond spray and I stopped on the fabric strop. That did help, but only for one or two shaves.

I certainly don't want to spend too much money keeping my blades sharp but would rather learn how and make that part of my routine/maint schedule. My goal is to use straights 100% of the time. I switched to safety razors of late though.

I ended up buying a pretty nice (in my novice opinion) Swaty Barber's Hone. I don't know the details but it was listed as a barber's hone. I got it today after it was missent and ended up in the next town over for a few days. I touched up both blades on this hone using this guide: http://www.youtube.com/watch?v=tP-GUeN_yBs. My great grandfather's blade (black scales) still pulled and still brought a tear to my eye. The Blue Steel blade (ivory scales) is the ticket! I shaved off my no-shave November (HAHA, it's almost two weeks into December) beard in under 20 minutes with just a couple nicks. Not bad after not using a straight for a few months, IMO.

How long should I expect to keep this newly touched up edge? 3-5 months? And how long will it take before I have to send it to a professional with all the proper hones to reset the edge?
Anyway, I remembered that the black scaled razor was always not as comfortable as the ivory one. Would the issue be the blade size? The condition of the edge? What could it be? I remember getting the black Morely back from restoration and thought it was good until I got the ivory scaled one and it was night and day difference.
I feel like I have the tools I need to keep a shave-ready edge on the blades (leather strop, fabric strop, Swaty barber hone). Please correct me if I'm wrong.
Or am I over thinking this and it's all normal?