New land/equipment quandary

So I'm buying another 20 acres next to me and need to change the way things are done. I have a full time job 50hrs a week plus in the summer. Currently I'm using a Massey 399 with a leley 8ft disc mower followed by an 8ft rake then a 426 baler. With what I have plus a new neighbor and 15ac plus new land coming online I'm torn as to what equipment I should invest in. The ground is clean minus gopher mounds. So I'm looking at a new Mowco or mower and rake. The Massey 399 is about 85hp so it is gonna be working hard for a new disc Mowco Moisture is not a big deal here. Most of the new ac is going in grass other than the bit I do in alfalfa Thanks

New land/equipment quandary