In the last 8 months I visited a good number of ICO pitches, the projects were primarily based and established in Singapore. My first impression was that a legal adviser in a Singaporean ICO is as much important as a founder. I agree with you that it's hard to find an adviser focusing on crypto  and there's no "crypto lawyer" as such, so far. However, as long as ICO/STO market is gaining interest from crypto communities and investors, the market itself and government start to react to this interest and "create" new requirements, for example, MAS guide to digital token offerings clearly states that a legal advice needed prior to deciding on a structure of a proposed digital token and a business model.

There are some minor signs of utilizing crypto as a payment way, but mostly cryptocurrency is a type of investment these days.
This tendency and perception will change with the time as the money world is actively migrating from a traditional to a digital form.

More and more companies around the world start to accept payments in cryptocurrency, including Bitcoin.
On the one hand, it is a revolution, but on the other hand, it's a coherent and consistent development of digital technologies.
Some sectors of used-to-be material world turn into a digital space.
It certainly brings new areas to explore and new knowledge to gain!

The thing is that nowadays all of us go through KYC and no one asks our permission. More than that most times we're unaware of the KYC being applied to us. When someone joins a new freelance platform as a client or as a tasker, or does an online purchase at a new online store, or registers a new account at any of those delivery apps - Menulog, Uber, etc - all these require a user to undertake a proper KYC. I'm sure most of you had to upload their driver's licence or any other ID or provide their bank/card details to initiate a simple process of delivery or payment. It is actually same KYC as the one done for ICO projects. The difference may be in complexity only but not the nature of the fact that we cannot say "no" to all those merchants, if we want our yummy pizza right now
Btw, there's a new era of KYC coming KYC for STO (!). This is going to be far more complex.

In terms of legal regulation - Switzerland would be the best one. Singapore is No.2 as the government set the guidelines in November 2017. I personally used the guidelines for a number of projects, they are pretty clear and precise.

In regards to your questions:
1. a number of times
2. Telegram, this forum
3. Team and advisers. I always do a good research on team, they should be able to deliver good development on the project.
4. Read thoroughly the whitepaper and road map. Once I find the concept vivid and applicable and the road marks feasible, I'm ready to invest.

What are the core team members and advisers you're looking at when judging on ICO? Does a reputable legal adviser change an overall picture? How can you check on their reputation?