Hey guys, sorry for the late reply, been busy lately. I've been considering all your advice and trying to get my hair closer to shaved, but still leave a bit on the top as well, just as a happy medium. For years I've been getting pretty much the same haircut style and for the past few years it has just looked worse and worse, so I'm really just trying to find out what works for me and my new hairline now. Like I said before I'm not ready to shave it all off at this point in my hairloss progression (because I know from my last experience I wasn't happy with it) so tell me what you think of the following haircut pics, what seems to work, what doesn't.
Few weeks ago I had a haircut I wasn't happy with:

You can see how when the hair is longer on the sides it really exaggerates my receding hairline. So I decided to go even shorter on the sides recently, and I wanted more taken off the top as well, but unfortunately she didn't take that much off the top and I didn't really realize it until later:



I tried to get some extreme side-shots in there so you can see where my hairline is at. Keep in mind all these pics are with the hair on the top swept forward a bit.
The following pics are from about a month ago with my hair longer:


While I enjoyed the comfort of having my hair longer, usually it just looked terrible, required way too much styling time to even look presentable, and there were many days where it was just completely un-manageable, and looked like crap.
My current game plan right now is just to find a haircut style that looks decent, continue with my treatments for at least another five months, and re-evaluate my results. I haven't had any side-effects at all with the Finasteride and Minoxidil and while I realize the effects over an extremely long time period are possibly unknown, at this stage in my life it is a price I am more than willing to take.
I know I sound overly narcissistic/vain considering my hairloss isn't extreme yet, but my hairloss has been gnawing on me for years, I know how fast it moves and I know it's only getting rapidly worse, so I really do feel justified in my vanity. There aren't many guys like us who even have to worry about MPB (particularly at this younger age), so I also feel justified in that regard.
I am however realistic about my self-image and about my hairloss in general. I don't want to look completely youthful forever, I just want to maintain a somewhat youthful appearance until I'm hopefully thirty. I don't want to give some sob story about how unfair my life has been--I had it so bad, boo-hoo--and now I'm balding. Life hasn't been a cake-walk for me, but I know it could've been much worse, I'm grateful for everything I've experienced, good and bad, and as Americans, we by default have it so good compared to the hell some citizens in other countries must live with. But suffice it to say, the circumstances of my life have made me feel that I deserve to keep some aspect of my youthful looks for as long as I can.