I think I understand what you're talking about, but I'll answer from several different angles just to make sure I cover your concerns.
If you're sitting at 149-150 F for a full hour before you pull the grain bag, etc., then raising the temperature towards a boil, fast or slow, will not hurt your fermentability at all really. If the mash sits at 149-150 F for (let's be extreme) zero minutes, you basically just get the grains wet and then immediately bring it slowly up to a boil over 20-30 minutes, then yeah, your fermentability will suck. Any mash greater than about 40 minutes will get you good fermentability. Quicker than that, and fermentability will suffer a bit.
Mashouts are pretty pointless for homebrewers. There's no need to bring things up to 170 F and hold for a few minutes for a mashout, if you plan to bring the whole wort up to boiling within like 30 minutes anyway, because then the mashout comes automatically in a timely fashion as soon as the wort hits 170+ F on its way up to the boil.
If you were to leave your wort sitting at 149-150 F for a long period while you perform a sparge, etc., then your fermentability will be high without a mashout. This comes into play for partigyle brewing where you might leave the first or second runnings to sit for an hour if you can't boil both partigyles at the same time. In these cases, a mashout might make sense especially for the smaller beer to prevent it from becoming extremely dry and watery.
It doesn't sound to me like you are doing anything outrageous, so I think the mashout is a moot point for you.
I should say, however, that I really don't think you need to rest your sparge water for 15-30 minutes. That's a complete waste of time. You can do a quick dunk, then immediately <2 minutes move your sparge liquid into the boil kettle.