Judgement in OS

One main issue here is when to pass on borderline hands.
There are several hand types and situations with which it is advisable to pass: Once we do decide to overcall, there are a few areas where the requirements for different calls overlap. These are summarized below.

Constructive auctions in OS

The main advice here is "don't worry about it too much". The strength ranges are so wide that it is difficult to build a good constructive structure. You are trading precision with the ability to interfere in "the opponents'" auction. Most of the time you will just rely on the Law of Total Tricks for your bidding decisions. If you use OS also when vulnerable, you will need to pay more attention to constructive auctions. On the good side, your ranges, especially for Simple Overcalls and NTO's, will be narrower.
See Constructive Overcall Structure Auctions for more detailed suggestions.