I was wondering what service people used for their Hobby Phone. Are there any you can actually activate from the phone anymore or do they all have to be done online or in a store? I've used tracfone in the past, but sometimes they randomly won't activate or re-activate.

To be most secure, activate from a library or something.  Use only cash to buy & add service time / minutes...  can be done from the handset.    
I wasn't that aware when I started...  I used my hobby email & a fake address.  The sky has not fallen...  though I will do differently on my next phone.  Mostly it is to keep one's regular phone 'clean' of tracks.  If you leave a dead body in the room when you leave, the subpoena to the phone company will triangulate your calls...    
If your lady friend gets busted, a misdemeanor...  even if they get her phone records, there's not an easy direct link to you.

and although I have & use trac as I said...  the market may have changed.  Even the big companies are getting into the prepaid business & know that none of the prepaid carriers owns their own towers.  They buy service on one of the big carriers towers.  Sometimes you can find out who prepaid company contracts with IN YOUR AREA...  if their contract phones het good coverage then the prepaid phones will too.  
In my area Trac has great coverage.  In another area, it might not.  My old phone ended up in a distant state & trac sent a different SIM card for it.

But like an idiot I bought the flip phone instead of one with a touch screen. It takes me 10 minutes to bang out a short text lol.  Bought it at target along with the minute card with cash. Very easy to register and don't need to provide any info.