Well i can say youre cheap on everything in my opinion. It may take you 3-4 times as long to mow and clean up the lawn, but think of the strain on your blades and motor with that tall thick crap. And not knowing whats buried in the lawn. As for the pruning to get things down to a manageable high, as you'l never get them to the size they should be at this point, you'll still be there for 3/4 of the day with just that. I'd be near a grand in my area for that job.
2011 f350 crew cab short box
1999 K3500 6.5
Stihl wackers/hedge trimmers
Little Wonder Vac/Walk behind blower