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U.S. financing structure using Lux Finco with MRPS (p. 629) [O]ne simple structure that was very popular — at least until the start of the BEPS initiative — used a Canadian parent to fund a Luxembourg subsidiary with mandatorily redeemable preferred shares. ... Still, this approach seems risky and may bump against the PPT antiavoidance rule in the proposed regulations. … [O]ther MNEs based in Canada (and elsewhere) might opt for a third approach that relies on simpler, non-hybrid, third-country financing structures. Some countries that have tax treaties with the United States — for example, Bulgaria, Hungary, Ireland, and Switzerland — have been carefully preparing for a post-BEPS world and offer very competitive corporate tax rates around 10 percent that may bring in business. ...

If A (a top-bracket Ontario-resident individual) owns Forco directly, the total tax payable is $767.65 ($500 foreign tax + $0 Canadian tax on FAPI + $267.65 Canadian tax on the dividend), for a tax rate of almost 77 percent on the initial $1,000 earned…The calculations are as follows: A has a $1,000 FAPI inclusion…. ... If the funds are to be reinvested by Canco, no Canadian tax arises, and the total tax payable is $500 of foreign tax… If the funds are to be passed on to A as a dividend for reinvestment at the personal level (instead of the corporate level), the total tax burden is $696.70[:] $500 foreign tax + $196.70 Canadian tax...calculated as 39.34 percent of the eligible dividend of $500. ...

. … Maarsman v. Canada (CRA), 2003 FC 1234 … recognized the "absurdity" of assessing interest during years when no taxes were owing and held in the taxpayer's favour on an application for judicial review. ... Slau Limited, 2009 FCA 270 ….] Application to Agreeing Provinces (pp. 1184-5)... ... The third clause of section 94.1 of the TAA – the privative clause – was added in 1996. ...

[F.n.420 – Lloyd F. Raphael, Canadian Income Taxation of Trusts, 3d ed. ... [F.n.421 – (1933), 1 DTC 243 (PC).] … The Privy Council concluded that on a true construction of the will there were three distinct trusts, which should be assessed and taxed separately. ... " [F.n. 424 … Supra note 420, at 270.] This statement was noted by the CRA in a technical interpretation…. ...

[fn 26: … 2009 TCC 118. para. 47.] More recently, however, in On-Line Finance & Leasing Corp. v. ... What we said in Haverty Realty & Investment Co., 3 T.C. 161, 167 (1944), still pertains today: The Supreme Court of the United States, almost all the Circuit Courts of Appeals, and this Court have held that the parol evidence rule cannot be invoked by a third party, not a party to the written instrument involved. ...

.$1,000, being the amount for which the common shares were issued (p. 5) [t]he Court found that "[t]he Indenture and the Prospectus [for the Debentures] clearly contemplate that the Common Shares are to be issued for US$14.00 per Common Share, which is equal to US$1,000 on a per Convertible Debenture basis …" And, further, "... in accordance with Teleglobe, this is the amount paid by Agnico for the extinguishment of the Convertible Debentures on the conversions. ... Ferran and Ho, in the same passage quoted above, add that "Cozens-Hardy [one of the judges on the Court of Appeal panel who concurred with Vaughan-Williams LJ. in separate reasons] expressly left open the question of a debenture issued at a discount to its par value which conferred a right at some future date to demand a fully paid share in exchange for the par value of the debenture. [... ...

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Furthermore, it did so expressly taking a practical business view of what would constitute a directing mind (expressed as " de facto control of both sides of the transaction"). ... First, the willingness of the courts to take into account relatively subjective business considerations, such as strength of bargaining power, in finding a directing mind seems to have carried the latter concept a long way. …. ... Wiffen Financial (p. 16:19) In Wiffen Financial Services [… 2003 TCC 780 …], the issue was whether an employment relationship was at arm's length, thus constituting insurable employment pursuant to the Employment Insurance Act. ...

. … To the contrary, in virtually every M & A transaction, the results of tax diligence are used primarily to inform the lawyers drafting the share purchase agreement as to what representations and warranties to demand, what covenants to seek, and the scope and structure of the indemnities required to adequately protect the buyer…This is the very core of the legal advice the buyer’s lawyers provide…. Commercial use of legal advice does not detract from it being legal advice (p. 3) [T]o some extent the court seems to conflate the separate questions of what constitutes the giving of legal advice and what the client does with that advice….Where a work product has been used by the buyer’s lawyers as an input to the legal advice they render, the client’s use of that legal advice to make a commercial decision should be irrelevant as to whether that legal advice (and the work product generated wholly or partially for that purpose) is protected from disclosure under solicitor-client privilege. … ...

. … S. 247 does not contemplate the OECD “accurate delineation” approach (pp. 21:13-14) [T]he 2017 guidelines permit the recharacterization of transactions on the basis of economic substance using the concept of accurate delineation. ... (p. 21:20) [T]he accurate-delineation approach under the 2017 guidelines … can be used, among other things, to characterize or recharacterize a transaction into an entirely different transaction with different tax consequences in a normal (as opposed to an exceptional) circumstance. These concerns are particularly acute in regard to controlled transactions between Canada and … the United States …. ...