Naive tax questions - there are no easy answers

Yesterday I mentioned a post on AccountingWeb in which my recent article was being discussed. The editor of Taxation magazine, Mike Truman, has contributed to the thread a couple of times, most recently in the context of, what I would call, naive tax questions. That is, straightforward questions clients might ask to which there are no straightforward answers.

I've copied Mike's list here and added 3 of my own to take it upto ten. I wonder if anyone can suggest any more:

1. How do I become non-resident?
2. More than 20% of the income of my company comes from letting an investment property, but the assets, time and expenses are all more than 80% trading. Will it qualify for entrepreneurs' relief?
3. As a sole trader, can I claim the cost of my lunches back when I am out on business?
4. I run a restaurant, and recently took a bottle of wine home to drink for my birthday. At what price do I have to account for it - the price on our wine list or the price in an off-licence?
5. And what about the bottle of wine I took home last birthday - do I have to account for that at anything more than cost?
6. My partner and I own a company in equal shares, but I have other income, I recently waived part of my dividend so that she could receive a larger one. Am I still taxable on it?
7. Rather than do A which would have given me a tax liability, I did B C and D, which had the same combined effect but with no tax liability, on a literal reading of the tax legislation. Am I liable to tax anyway?
8. How much tax will I save if I incorporate my business?
9. How much of my car costs, mobile phone costs, home related expenses etc can I get off my tax?
10. I'm not domiciled in the UK, is it worth me paying the £30k bung?
    

Going back to the point I made yesterday, the danger comes when someone attempts to answer such questions without first seeking clarification of the surrounding facts and without adding the necessary caveats. If a tax specialist who understands such issues would consider this necessary, I'm sure no generalist adviser would take a more relaxed view. Would they?

In any event, let's see how far we can extend this list.