so to answer a few of your questions.
the bike is a Spalding Blade my dad bought from Sears. i had this bike since i was 13 years old, it will always be with me and ridden. it has taken me so many places in my life and has many more to take me. I just started ridding again in april and just "fixed" this bike in may.
the things that have broke this year;
1. pedal bent while standing and mashing up a incline, limped it to a bike shop
2. Chain snapped sprinting from a stop light. wife had to pick me up.
3. seat post kept getting loose (the part the grabs the saddle rails) and the seat would just move all over. end up limping home
4. seat post thingy finally stripped and had to ride standing up till wife came and got me.
5. after three rides handle bars keep getting loose and i almost kill myself when i stand to sprint and the bars rotate. limp home again
6. wheels go out of tru each month. wife hate me truing them in the living room.
7. noise from the bottom bracket that i will check this winter.
8. brakes need bi weekly adjusting (single pivot calipers)
its nothing really major and most of it is because my *lack of wrenching skills
and wife complains i am always working on it or fixing something on it.
the bike has always been to big for me and my last growth spurt was at 16 and i never grew into it. after 25 miles its uncomfortable. stem shifting SUCKS, it really SUCKS. its not bad when i get out of the city where there are less stop lights but most of my riding is in the city.
the condition of the $500 is its not cash and cant be used on the old bike (last one is per wife). I am leaning toward the Gravity with Apex the more i think about it. but the apex is its only selling point the rest seems like cheap and no name components.
BTW, i do have another bike a beach cruiser which is my dedicated commuter and errand bike.