1. There is a huge chandlers down in Port Solent that sells all waterskies , ringo etc at reasonable prices aslo a nice place to go for lunch.
2. I have towed skiers for many years but never had proper training, take it slow and make sure you have a good look out for the skier, practice picking up using the figure of 8 turn to retrieve the skier, may be an idea to practice this using a fender instead of a skier for the first few attempts.
3. I ski in Alum bay which has good shelter and you can get close to the shore as the bank has a steep drop on it , or go across Poole bay to studland bay which is very nice and great for sking etc.
4. Lymington is a good place to keep the boat but i dont think you will get in now. Maybe Chchester or Hayling island would be a good bet to moor the boat. As long as you use the boat regulary yoou wont need to antifoul it, whe you take the boat outto the beach take a scrubbing brush and clean the hull as best you can, regular use will remove algi etc,
5. A boarding lader will help you get back in the boat which is not easy when you are tired after sking.
Hope this is of help.