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If some awful things happen where actual money would help, how would you feel if it's been sunk in paying off a house with no way to reborrow the money ?

Actually, he's already made some of his assets illiquid:

I remortgaged my house and bought a small mixed use property for cash...

OP, you have more than a tax question. You have a financial planning situation. Meet with someone from www.napfa.org, and bring a list of:
1. Goals (e.g., early retirement, children's college, etc)
2. Assets (and how each is titled)
3. Cash flow (income and expenses; add 'em up for the past 12 months)
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