Is it suppose to hurt?

You might try this http://www.gigbasics.com/jamplug.html I've been considering getting one to practice late at night, since I'm a night person and my wife goes to bed early.

Ok SOB-N, so most of your questions have been answered but i'll chip in anyway. Yep the fingers are gonna hurt bad when you just start playing until you develop callouses on the tips - and even then, they could still hurt after playing long stretches often.

I also have a dreadnought shaped acoustic/electric, but no amp yet either. I'm not keen to get one right now since I haven't started playing out or with a band where I need to be heard over noise or other instruments. Plus my neighbors probably wouldn't appreciate it - i think my unplugged sessions drive them crazy as is.

..... by the way, mine is a Takamine G-series - pretty loud even unplugged

You might try this http://www.gigbasics.com/jamplug.html I've been considering getting one to practice late at night, since I'm a night person and my wife goes to bed early.
Man that is great. I don't get home from work till 9 at night. One of those would be great to jam with then, and it's only $40 bucks. I see a potential Fathers Day gift here.