Parker, I would first get up and on the air with your antenna as high as possible with the best quality antenna you can afford. That said you might look at the antennas at A-1 on the bottom section of the forum here, they are exellent.
When you do decide to get some power you must consider what you want to spend, tubes or transistor,how much power you are looking for, and if it is transistor are you going to run a mobile on a power supply or an actual base amp that plugs into the wall.
That said just remember, a guy with a great antenna 100 feet in the air straight radio will whipp your tail on a cheapo antenna 30 feet in the air even with say 250 watts. And with your 250 watts low to the ground you might be getting into all your neighbors stuff as well.