Recently, there has been an increasing interest in the development of an approach to characterize the as-built heat loss coefficient (HLC) of buildings based on a combination of on-board monitoring (OBM) and data-driven modeling. OBM is hereby defined as the monitoring of the energy consumption and interior climate of in-use buildings via non-intrusive sensors. The main challenge faced by researchers is the identification of the required input data and the appropriate data analysis techniques to assess the HLC of specific building types, with a certain degree of accuracy and/or within a budget constraint. A wide range of characterization techniques can be imagined, going from simplified steady-state models applied to smart energy meter data, to advanced dynamic analysis models identified on full OBM data sets that are further enriched with geometric info, survey results, or on-site inspections. This paper evaluates the extent to which these techniques result in different HLC estimates. To this end, it performs a sensitivity analysis of the characterization outcome for a case study dwelling. Thirty-five unique input data packages are defined using a tree structure. Subsequently, four different data analysis methods are applied on these sets: the steady-state average, Linear Regression and Energy Signature method, and the dynamic AutoRegressive with eXogenous input model (ARX). In addition to the sensitivity analysis, the paper compares the HLC values determined via OBM characterization to the theoretically calculated value, and explores the factors contributing to the observed discrepancies. The results demonstrate that deviations up to 26.9% can occur on the characterized as-built HLC, depending on the amount of monitoring data and prior information used to establish the interior temperature of the dwelling. The approach used to represent the internal and solar heat gains also proves to have a significant influence on the HLC estimate. The impact of the selected input data is higher than that of the applied data analysis method.