Though this will be for commuting purposes, I ride (and prefer) hybrids. Also feel I won't get as many recommendations to "just get a road bike" here- which some of y'all know my background and the reasons why drops aren't in my future.

Now down to business. I've got a couple of job leads the next town over- could be anywhere from 9 to 15 miles. 99% of the time, I'd be on some variation of asphalt. And there are hills. I can (and have) ridden the route once and could do it for the near term. However, I've since come to the conclusion that my bike is just a tad too big, and really hoping to get another bike that fits me better.

That being said, I'm wondering if I should keep an eye out for bikes that have road gearing or mtb gearing? Mind you, I already tend to gravitate towards the performance/fitness side of the hybrid spectrum, but I also like to coast.

How big are the hills?

You can always change the gearing.

Often, what comes on a new bike is something that everybody can use some of the time.
IF you are commuting, you really don't need a lower gear than your worst hill, or a higher gear that can only be used with a 60 MPH tail wind.

Both my bikes are triples with a 12-21 & 12-23 cassette and 22-32-38/36 rings
My normal starting gear is M1.
IF I were to do a hill or EXTREME headwind, I have the granny ring.
If I get a tailwind or a chance to "cruise", I go to the big ring.

I really don't think you will need MTB gearing...stick to the road gearing and for the climbs, just build some speed so you wouldn't have to pedal so much once you do climb.

My current gearing is 42/34/24 and 11-32 8spd in back, and I usually ride only using the 42 and 5 highest gears in back. I really don't need too much more at the top end, as anything over 25 mph or so makes it too hard for me to visually process everything, but I've always felt like the gearing was way too low.

As far as the hills go, they pale in comparison to some, but I'm still not in the best of shape, either- and 20 mph headwinds aren't unheard of. I don't know how to find the elevation/topographical info, but if you wanted to look it up, be my guest. Starting point would be Sapulpa, OK 74066 ending at Sand Springs, OK 74063, following the OK 97 corridor.

Thats more than enough gearing..im at 26/36/48 and almost never go on my granny gear. You should be fine. As far as strength..the only cure for that is to keep riding. no shame in walking and eventually you will ride over everything once you have ridden on them enough times.

It's very personal and it depends on your average cruising speed and hill climbing power.
Even in road gearing there are many different options.
Anything from compact or even a triple 50-39-30 with 14-28 to a double 53-39 with 11-21 cassette
Pich the one you like best.

If your cassette was like the one that came on my 2008 Specialized Globe, it was-
11-13-15-18-21-24-28-32
I absolutely hated it. I didn't need the 2 largest cogs and the 3T jump from 18 to 15 would almost blow my knee out.

I've since gone to a 12-23 9 speed with a 22-32-36 crank. (Emphysema prevents me from being able to use any higher gears)
Before going to the 9 speed I made up an 8 speed with some spare cogs I had laying around.
12-13-14-15-16-17-19-21.

IF you very seldom use the 11T cog, I'd suggest an 12-23 cassette. You could try your 34-24 combination to see if that seems suitable. Also if 24-24 will get you up all your hills, the 23T is only a bit higher.
12-13-14-15-17-19-21-23.