Probably not, although I'm not sure I understand your plan. Do you mean (") inches, or (') feet?
The acceptable length of cable varies by how "hot" the signal is at the tap or splitter on the pole. Higher frequencies attenuate faster than low frequencies. An example of this can be seen on analog systems where the high channels go grainy, while the lower channels are just fine.
The problem with putting an amplifier at the end of a long run is that you are amplifying crap. The amplifier needs to be inserted before the signal turns to crap.
Here's the attenuation for some nice RG11 direct burial (Commscope): »www.commscope.com/catalog/unipri ··· id=34377
If internet is your main goal, you'll be most concerned with 567-585 MHz area.
"Back in the day" when I was working for the cable company 150' was pretty much the limit on RG6. They didn't like RG11 going beyond 250'.
If you insist on trying it yourself, Here's what I would do:
I'd run 200' of RG11 from the pole to a pedestal:»www.telephonecentral.com/Product ··· 203.aspx
(you could probably just use a 12 X 12 PVC box on strut)
I'd place this amplifier in the pedestal:
»www.dropamp.com/shop/product_inf ··· ts_id=28
The amp will be LINE POWERED from the house (this means the coax will also carry the power). You'll need the matching power supply and power inserter: »www.dropamp.com/shop/product_inf ··· ts_id=40
Then bury the next 200' of RG11 to the house.
Of course, you would need to discuss this plan with Charter, as they normally own, and are responsible for, the outside drop.
Before attempting any of that, I would attempt to negotiate a lower installation price with Charter and put the onus of installation on them. Maybe remind them about your initial conversation and offer to sign a 2 year deal.
By the time you are done with all the rigmarole of a DIY long distance drop, it may be cheaper to have Charter do it. With the cost of wire, fittings, amps, enclosures, and most importantly - your time; is it really worth it?--
If someone refers to herself / himself as a "guru", they probably aren't.