IIRC, the Romney campaign said after the fact in 2012 that Obama's ad buys really did them in in a couple of states - specifically early-morning ads targeted at the elderly. It appears Trump didn't learn this lesson.
I'll like to make an observation:
If Clinton can lock up FL, WI and PA, she wins.
If she locks up FL, WI and OH, she wins.
If she locks up FL, WI, VA and NV, she wins.
WI looks to be gone for Trump. FL looks to be trending away from Trump. I know I would rather be in Clinton's position right now. They are definitely going for the kill in FL.
Trump is raising money, but how much of that money is going to go to ads and ground game?