We investigate nearside stellar-driven outflows from the Large Magellanic Cloud (LMC) using UV absorption-line spectroscopy of 170 OB stars, complemented by HI 21-cm emission and H_α emission. Using Voigt-profile fitting and AOD analysis of SiII, OI, and SII transitions, we map the velocity-dependent structure of foreground gas. The SiII column densities for the Voigt-fitted components decline smoothly from the LMC disk and reach a minimum at v_(rm LMCSR) ≈ -100 to -200 km s⁻¹, marking the transition from a denser, slower wind to more diffuse high-velocity material. Comparisons with local star-formation rate surface densities reveal a modest positive correlation for the slower wind component, linking it to recent massive-stellar feedback. Photoionization modeling of 13 absorbers in the +100≲ v_(rm LSR) ≲ +150 km s⁻¹ range reveals wide diversity in metallicity, dust depletion, and ionization conditions, consistent with multiple possible origins. While a substantial fraction of this predominately ionized gas is consistent with the high-velocity extension of the LMC wind, part of it may arise from contamination by Milky Way (MW) high-velocity clouds (HVCs) and Magellanic circumgalactic medium (CGM). We estimate a nearside cool-gas outflow mass of ∼1.8×10⁷ M_⊙, implying Ṁ_(rm out)≈0.15-0.33 M_⊙ yr⁻¹ and a mass-loading factor of η≈0.6-1.3. On regional scales, 30 Doradus contributes ∼10% and N11 contributes ∼3% of the total outflow mass, while the trailing side contains more wind material than the leading side, consistent with ram-pressure stripping. These results provide the comprehensive kinematic and physical characterization of how stellar feedback, galactic environment, and foreground contamination shape the multiphase wind emerging from the LMC.