I did something similar to what the O. P. is doing.
Bought the shoreline property a lot down from ours on a foreclosure auction for about what the lot was selling for at the time. I tore down a 28' X 24' section but decided the remaining 1400 SF was salvageable. I stripped the interior to the studs and replaced all the floor joists and subfloor, as well as a new furnace and wiring, and improved drainage.
I did the dump truck and skid steer route, rather than the dumpster scenario, as I am doing this part time. My truck is an F450 with an 8' dump bed. License and insurance runs around $500 / yr. from memory, and it gets around 7-9 mpg on my dump runs, and 6-7 mpg hauling fill. The transfer station is 30 miles round trip and a load runs from $7.50 (cheapest, 90% insulation) to $130 (most expensive, roofing materials) to tip. I have a stack of receipts an inch thick, probably a couple of thousand dollars worth, and I only went to the studs for most of the building. Putting the debris out with the trash is futile. You'll be at it until the next millennium.
The $8000 quote is an excellent deal. You will need permits for demolition, and asbestos remediation is a real possibility. In my case, the house was from the late sixties, so asbestos was ok. You will also have to hire help for the demo, especially since the house is so close to your residence and it is a two story. Budget a couple grand additional for that, and make sure whoever you hire has insurance. You should have liability insurance too, although you may be able to add it to your existing property if it is contiguous. In my case, the property is separated from my home by a 100' lot that is owned by someone else, so it requires a separate policy.
You cannot burn, nor can you burry the demo debris as some propose, probably because of the lead paint and toxic chemicals (plastics, etc) that will undoubtedly be there.. The inspector may want to see your transfer station receipts to prove you disposed of the debris properly.
In my case, I'll end up with a nice summer and possibly winter / snowmobiler lakefront rental, and , as stated I'm in no hurry, so it makes a little bit of sense to do the demo myself. Got a real nice "spare" 24'X32' garage out of the deal too.
Have fun!