Purchasing a new backhoe. Input and also to buy with 4-1, or upgrade with a 4-1?

Looking into purchasing my first backhoe, been researching/watching local for sale for about 6 months now. I run a farm and need to remove a lot of trees, trench and lay new waterlines/french drains, build 2 barns, and change the layout of the land a bit. I've been doing what I can with a 90hp DX90 tractor but no FEL and limited into what I can do with it. Im leaning towards a Case 580k or SK (preferably with a cab that I could upgrade with AC) as they seem to be a little cheaper then JD and...

Purchasing a new backhoe. Input and also to buy with 4-1, or upgrade with a 4-1?

Purchasing a new backhoe. Input and also to buy with 4-1, or upgrade with a 4-1?