Well I sort of see this as the opposite issue. Bill didn't want to pay a lot of lineman, and now we have a lineman problem. Bill didn't want to pay WR's and we have a WR problem that's persisted for years. Bill didn't want to make a good offer to Brady and made him feel unappreciated, and we have not had decent QB play since. Then we overpayed a bunch of old guys on defense from the last dynasty like Hightower/McCourty/Chung and watched them all decline. Like we could have just paid Cooks, Thuney, Meyers etc and minimized a lot of our biggest problems the last few years.
We didn't value good players enough to keep them and let problems develop and when we did, it felt like we paid Bills boys for loyalty. When Brady was here, that was minimized. But a point came when Brady was sick of it and thought he could be more competitive somewhere else.
The other issue was not accepting the reality of where the team was at and that we needed to build for the future and not try to plug and play thinking it would help get us through the year.