Howard Leight Earplug Instruction Poster.
Following the directions on that poster makes the difference between the middle and right pictures below (which is probably 5 dB NR in the left picture, 12 dB NR in the middle picture, and the full rated 32 dB NR in the right picture) Seriously, if you've never thought you were going to need a tweezers to remove an earplug you're probably doing it wrong.

I always double up at the range using properly inserted foam plugs under my 25 dB NRR passive muffs; 9 out of 10 times I use foam plugs when running outdoor power equipment as well.
According to this article from AudiologyOnline.com
...which is still a significant and meaningful improvement over either plug or muff used alone.Note for example; at 1000 Hz the combination of a 26-dB plug and a 34-dB muff does not yield 60-dB overall, but rather about 41 dB.
To meet your requirements of very good hearing protection, under $350 for matching his & hers sets of hearing protection, and being able to carry on conversation with all hearing protection in place; my best suggestion would be doubling up something similar to the 30 NRR Howard Leight electronic muffs that Hmac mentioned, along with a passive filtering ear plug like E.A.R. Inc HearDefenders, New Dynamics/3M "Combat Arms Earplugs", or Health Enterprises "Shooter's Impact Noise Reducing Ear Plugs".
All this looking at hearing protection has me thinking about a few upgrades for myself. Since I'm due for a bulk order of foam ear plugs anyway I might have to see if I can improve upon my standard hearing protection strategy.