Background/Objectives: Dental implants have emerged as a modern solution for edentulous jaws, showing high success rates. However, the implant’s success often hinges on the patient’s bone quality and quantity, leading to higher failure rates in poor bone sites. To address this issue, short implants have become a viable alternative to traditional approaches like bone sinus lifting. Among these, Bicon® short implants with a plateau design are popular for their increased surface area, offering potential advantages over threaded implants. Despite their promise, the variability in patient-specific bone quality remains a critical factor influencing implant success and bone turnover regulated by bone strains. Excessive strains can lead to bone loss and implant failure according to Frost’s “Mechanostat” theory. To better understand the implant biomechanical environment, numerical simulation (FEA) is invaluable for correlating implant and bone parameters with strain fields in adjacent bone. The goal was to establish key relationships between short implant geometry, bone quality and quantity, and strain levels in the adjacent bone of patient-dependent elasticity to mitigate the risk of implant failure by avoiding pathological strains. Methods: Nine Bicon Integra-CP™ implants were chosen. Using CT scans, three-dimensional models of the posterior maxilla were created in Solidworks 2022 software to represent the most challenging scenario with minimal available bone, and the implant models were positioned in the jaw with the implant apex supported by the sinus cortical bone. Outer dimensions of the maxilla segment models were determined based on a prior convergence test. Implants and abutments were considered as a single unit made of titanium alloy. The bone segments simulated types III/IV bone by different cancellous bone elasticities and by variable cortical bone elasticity moduli selected based on an experimental data range. Both implants and bone were treated as linearly elastic and isotropic materials. Boundary conditions were restraining the disto-mesial and cranial surfaces of the bone segments. The bone–implant assemblies were subjected to oblique loads, and the bone’s first principal strain fields were analyzed. Maximum strain values were compared with the “minimum effective strain pathological” threshold of 3000 microstrain to assess the implant prognosis. Results: Physiological strains ranging from 490 to 3000 microstrain were observed in the crestal cortical bone, with no excessive strains detected at the implant neck area across different implant dimensions and cortical bone elasticity. In cancellous bone, maximum strains were observed at the first fin tip and were influenced by the implant diameter and length, as well as bone quality and cortical bone elasticity. In the spectrum of modeled bone elasticity and implant dimensions, increasing implant diameter from 4.5 to 6.0 mm resulted in a reduction in maximum strains by 34% to 52%, depending on bone type and cortical bone elasticity. Similarly, increasing implant length from 5.0 to 8.0 mm led to a reduction in maximum strains by 15% to 37%. Additionally, a two-fold reduction in cancellous bone elasticity modulus (type IV vs. III) corresponded to an increase in maximum strains by 16% to 59%. Also, maximum strains increased by 86% to 129% due to a decrease in patient-dependent cortical bone elasticity from the softest to the most rigid bone. Conclusions: The findings have practical implications for dental practitioners planning short finned implants in the posterior maxilla. In cases where the quality of cortical bone is uncertain and bone height is insufficient, wider 6.0 mm diameter implants should be preferred to mitigate the risk of pathological strains. Further investigations of cortical bone architecture and elasticity in the posterior maxilla are recommended to develop comprehensive clinical recommendations considering bone volume and quality limitations. Such research can potentially enable the placement of narrower implants in cases of insufficient bone.