So, how heavy of a tractor have you guys used and not had bad problems with lawn rutting or how heavy was "too heavy" for you for finish mowing? .... I want to know if buying that next size up is going to cause me any additional issues other than financial
My two cents ... it depends. I think it really is site specific; a tractor than works just fine one place may cause damage somewhere else. A friend back east tells me his JD 3320 TLB tears up his lawn pretty easily, especially if there's been a recent rain. On my "lawn" that 3320 wouldn't bother at all. There are big ag tractors (8000 series JD and similar size CaseIH) that cross places I mow near our property to get to the fields that do surprisingly little damage. Minimal rutting and a mowing or two later, you'd never know they had been there but on the other hand there were spots on my folk's place back in Maine that a little Ariens YT-11 lawn tractor would tear up.
Type of soil and how well it drains, vegetation, terrain (hills, low spots, nearby creeks and/or ponds etc.) all enter into it. Around here the orange and green dealers will let you try before you buy- if your dealers do the same I'd go as big as you and your budget can stand/want to and work down from there.