casemark/analyzing-m-and-a-tax-implications

Analyzing M And A Tax Implications

Evaluates tax implications of acquisition structures, comparing asset vs. stock purchases, Section 338(h)(10) elections, Section 368 tax-free reorganizations, and basis step-up opportunities to identify the most tax-efficient deal structure.

When To Use

• Buyer or seller needs a comparative tax analysis of proposed acquisition structures
• Evaluating whether a 338(h)(10) election yields net tax benefit over a straight stock purchase
• Determining if a transaction qualifies as a tax-free reorganization under Section 368
• Quantifying the present value of basis step-up through amortization/depreciation
• Assessing cross-border deal structures with international tax overlay (GILTI, BEAT, Subpart F)
• Pre-LOI structuring advisory or post-LOI tax diligence support

Inputs To Gather

• Deal parameters: Purchase price, proposed structure (asset/stock/merger), target entity type (C-corp, S-corp, partnership, LLC)
• Target financials: Balance sheet with FMV estimates for key asset classes, inside vs. outside basis positions, net operating losses and credit carryforwards
• Seller profile: Shareholder composition (individuals, trusts, tax-exempts, foreign holders), holding periods, prior Section 338 elections
• Buyer profile: Entity type, existing NOLs, acquisition financing structure (debt/equity mix), strategic vs. financial buyer status
• Asset detail: Tangible asset classes with estimated useful lives, identifiable intangibles (customer lists, IP, covenants), goodwill estimate
• Jurisdiction data: State/local tax rates for buyer and seller, nexus footprint, apportionment factors [VERIFY state-specific rules]

Workflow

1. Classify the target entity and deal type

   • Determine target entity tax classification (C-corp, S-corp, partnership, disregarded entity)
   • Map proposed deal mechanics: direct asset purchase, stock purchase, statutory merger (forward/reverse), or equity interest purchase
   • Identify whether Section 338(h)(10) election is available (requires target to be S-corp or member of consolidated/affiliated group)

2. Model the asset purchase scenario

   • Allocate purchase price across IRC Section 1060 asset classes (Classes I–VII)
   • Calculate depreciation/amortization schedules for each asset class (Section 168 for tangibles, Section 197 for intangibles/goodwill)
   • Compute present value of total tax shield from step-up using buyer's discount rate
   • Identify state-level conformity or deviation from federal asset allocation rules [VERIFY]

3. Model the stock purchase scenario (no 338 election)

   • Buyer acquires stock at cost basis equal to purchase price; no step-up in target's inside asset basis
   • Identify trapped tax attributes: NOLs subject to Section 382 limitations, built-in gains/losses
   • Calculate Section 382 annual limitation (long-term tax-exempt rate × equity value of target) [VERIFY current applicable federal rate]
   • Assess successor liability exposure and its tax implications

4. Model the 338(h)(10) election scenario

   • Treat the stock purchase as a deemed asset sale for tax purposes
   • Calculate deemed sale price (ADSP) using the formula: purchase price + target liabilities + tax on deemed sale
   • Run iterative tax calculation (deemed sale tax is circular — the tax affects ADSP which affects the tax)
   • Allocate ADSP across Section 1060 classes to establish new inside basis
   • Compare buyer step-up benefit against incremental seller tax cost; determine net deal benefit and who bears it

5. Evaluate Section 368 reorganization qualification

   • Test applicable reorganization type: Type A (statutory merger), Type B (stock-for-stock), Type C (stock-for-assets), or triangular variants
   • Verify continuity of interest (COI): at least 40% of consideration must be acquirer stock (based on IRS ruling guidelines) [VERIFY current COI threshold]
   • Verify continuity of business enterprise (COBE): acquirer must continue target's historic business or use a significant portion of target's assets
   • Assess boot received by target shareholders and resulting gain recognition under Section 356
   • Identify potential disqualifying elements (cash consideration exceeding limits, step-transaction doctrine risks)

6. Cross-border and international overlay

   • If target has foreign operations: evaluate GILTI inclusions (Section 951A), Subpart F income, and Section 245A dividends-received deduction
   • Assess BEAT applicability if post-acquisition base erosion payments exceed thresholds [VERIFY current BEAT base erosion percentage threshold]
   • Review treaty implications for withholding on cross-border payments
   • Evaluate Section 367 toll charges on outbound transfers of assets to foreign entities

7. Comparative structure analysis

   • Build side-by-side comparison matrix: asset purchase vs. stock purchase vs. 338(h)(10) vs. 368 reorganization
   • Quantify after-tax cost to buyer and after-tax proceeds to seller under each structure
   • Calculate net present value differential across structures
   • Identify structure-specific risks: successor liability (asset vs. stock), Section 382 limitations, recapture exposure
   • Flag purchase price allocation sensitivities and negotiation leverage points

Output

• Structure comparison matrix: Side-by-side table showing total tax cost/benefit for buyer and seller under each modeled structure
• Step-up analysis: Asset class allocation with depreciation/amortization schedules and PV of tax shield
• 338(h)(10) analysis: ADSP calculation, iterative tax computation, and net benefit quantification
• 368 qualification assessment: Pass/fail on each requirement (COI, COBE, boot limits) with supporting rationale
• Recommended structure: Identification of optimal structure with quantified tax savings and key assumptions
• Risk flags: Successor liability, Section 382 limitations, recapture triggers, state nonconformity issues

Quality Checks

• Verify Section 1060 allocation sums to total purchase price (no residual gaps)
• Confirm 338(h)(10) circular tax calculation converges (iterate until delta < $1)
• Validate Section 382 limitation uses current long-term tax-exempt rate [VERIFY]
• Cross-check that 368 analysis addresses all statutory requirements for the specific reorganization type claimed
• Ensure state tax analysis covers all jurisdictions where buyer and target have nexus [VERIFY state conformity with federal elections]
• Confirm discount rate used for PV calculations is consistent with buyer's weighted average cost of capital
• Flag any assumed asset FMVs that lack appraisal support as [VERIFY]