1. I cant help with

2. and 4. are pretty much the same (2. being the easy option)

3. well have a go at 2. first then you know how much to pay someone ;-)

 

think of the hair as lots of strips laid on a swim cap

what you need to do is select the frst row (nearest cap) and set them as constrained

could do that in poser using grouping tool (might drive you mad)

could do it in your modeler maybe a bit easier

now I dont know if after doing all that you will get the results you want , some hair it might work ok some it deferantly wont

might be better for you to look for dynamic hair