At what point will I need better skates?

[Loops]

You'd agree that being able to get my finger between the back of boot and heel means too big?

Yes.

[sarahspins]

It was a Jackson stick. I used the women/children's side not the mens. I am an 8 shoe, measured between 7-7.5, have a 7 skate and when I push my foot all the way forward over the rocker I still can fit one finger all the way down the back of the heel.

The sizing stick isn't always 100% reliable in predicting size and fit - at best it is just a good starting point.

I usually wear an 8 street shoe (sometimes a 7.5) and I wore a 6.5 Jackson in a split width and was very happy with them.  When I was fit initially, a 6C was too short and much too tight around the ball of my foot (and we only tried the 6 because my prior pair of SP Teri customs were 6's) - I never tried a 7, but I suspect it would be too long since I was very happy with the length in 6.5's I tried, and even happier with a split width (I've had two pairs with an E ball and B heel).  Honestly I'd still be in Jacksons if they hadn't changed their boot line making the options I need a full custom instead of just a modified stock boot (I am allergic to latex, which means that grey foam used on most boot tongues is a no-go for me, and custom tongues + split width is a $$$ extra fee with Jackson after they discontinued the 3900 boot which had covered tongues). My custom harlicks are split sized, my left is about 6.75 and my right is 6.5 - now that my boots are well broken in, I do feel like I have a little bit too much room in the toes on my left though, but some of that could just be because the insoles are different in both of them as well, I have a wedge in my right boot that takes up a little more room than the normal insole in the left does.  It's worth noting that it hasn't caused any problems while skating - it's more of a "my foot doesn't feel right" issue, but nothing on the ice has been effected by it.

[jlspink22]

Why oh why couldn't I have normal B width feet!

[sarahspins]

I think most skaters don't have "normal" feet - it's all relative, really

Fit is just far more critical in something like skating boots than it is in street shoes.

[jlspink22]

I went back in the shop and tried on higher level Jackson's in 6D, too wide in heel and too short but ball width was good. Also tried sz 6 reidells in a M, which felt really good except a tad too narrow in the ball. I'm assuming my toe needs to brush the end of the boot without scrunching up.

[Loops]

I went back in the shop and tried on higher level Jackson's in 6D, too wide in heel and too short but ball width was good. Also tried sz 6 reidells in a M, which felt really good except a tad too narrow in the ball. I'm assuming my toe needs to brush the end of the boot without scrunching up.

I think the toes, to a degree, is personal preference.  I personally don't like to feel the very front of the boot, but you don't want to err on being too long.
 
Something to think about- when I bought my last pair of running shoes, the guy told me that feet swell as you run (so they always put you in bigger shoes than you think you need).  I'm guessing the same thing happens in skates, because for me boots that feel either OK/ smidge too narrow, turn out to be uncomfortable/painful during skating.  Thank heavens for punching out! 

Perhaps others can comment, but in light of my experience and what the runner guy told me,  I would definitely avoid anything that already feels tight, let alone "a tad" too narrow in the store.   

[jlspink22]

I wore trouser socks (like tights more than socks) and 7 was far too big even after skating for an hour so I think a 6.5 would be perfect lengthwise.

[aussieskater]

I'm assuming my toe needs to brush the end of the boot without scrunching up.

Agree with loops that toe length is a matter of personal preference, but your toes absolutely mustn't scrunch up - that means the boot is too short.  They also shouldn't be forced to fold over each other or lie on top of each other - that means the boot is too narrow in the toe box.  Ideally, your toes need to be able to lie flat in both directions (length and width) and wiggle a bit.  The "a bit" is a matter of personal preference  .

[artist007]

I agree, I think they're too big too.  Your skate should feel snug, but not uncomfortable.  There is a website that has a wealth of skating information on fit, skates comparable for skill levels etc.  You might want to check there and ask questions.

http://www.iceskatesnblades.com/guide-to-buying-new-skates.html

http://www.iceskatesnblades.com/measuring-feet-for-skates.html

https://www.kinziescloset.com/skate-comparison-guide.html