Well, it's finally time to tackle this wee problem, now that I've a signficant other! I hope you fine folks can be of service to a bashful late bloomer~
I have a very tight, droopy overhanging foreskin, since as long as I can remember. For a long time I didn't even realize foreskins were supposed to be pulled back, and I thought it was normal, so I never got used to the idea, and now it's essentially stuck like this (see image). Now I realize how unhygienic and generally unwise it is, but I've got a bit of an issue pulling it back (thank god I DIDN'T need to get circumcised like the first doctor insisted). I know it's possible since I did go see a doctor about it a few years back and he did pull it back manually, but I haven't been able to really do so myself without feeling very uncomfortable.
I guess my question is what I should do to make it less tight? Thanks 
(Note: I currently live abroad, so I don't know if I'll have a ton of luck finding whatever medicine/specialist might be recommended, but I'll try my best)
Whoa! The feeling on circumcision seems to be totally polarised and while I would agree that uncut is best there are times for intervention. It is - of course - permanent and will - if done properly - be 100% effective. A less radical option is a dorsal slit which makes a slit through the top of the foreskin and can be effcetice albeit giving a slightly odd appearance. Google it for further information. If the skin is really tight it is a condition called phimosis. Some say that it is possible to have a satisfactory sex life with this but there are dangers of tearing [which will make things worse when it heals if it scars] and it may be a medical emergency if the foreskin gets trapped behind the glans and will not go back.
It would be interesting to hear a woman's reaction in this case. Certainly you have identified a potential hygiene problem ...
There are said to be effective creams that you can use but these would be on prescription [in UK anyway]. I think the answer is to find a doctor who can consider other actions other than the simple one of circumcision in whatever country you are. If you are able to obtain specialist advice then a good urologist would be your best bet!
Although not particularly pleasant in my day [think dinosaurs] there was a school medical service which examined school boys [etc] and would have identified any "problem" at an early age.
I'm not really sure what I'm looking at? What's the skin tag sticking put on top? So basically the hole that the foreskin makes rolling over the head of the penis, essentially closed up?
May I ask how you were able to take care of yourself w out hurting yourself? Sounds like what Simon said, you may very well need to have some skin removed to at least open it up more AMD it not require a full circumcision
Archemedes will need to comment on this, because he's a doctor and he would know more about this than I certainly.