Property market value and per door cash flow

I am a new investor, and am interested in purchasing a multi-family residence and house-hacking in the Boston, MA area.

Does a direct relationship between property market value and monthly cash flow exist? In other words, do more expensive properties clear a higher dollar per door rate, or do operating expenses scale proportionally (or are repairs and CAPEX so volatile that it is hard to draw the conclusion)?

Outside of this question, what are your thoughts on more expensive properties vs. cheaper properties for a first-time investor?