So how are they going to go about doing this with all the stuff from houses in the way as they want to four lane it one day as well to Union City which will continue to El Reno. It's similar to the Duncan Bypass which now is receiving it's south side connector but is to be limited access as well one day they may four lane it.
Just about any new highway project will require buying and clearing at least some properties in the path of the highway alignment.
For reference, here's a link to a PDF showing the alignment of the proposed Chickasha bypass:
http://www.okladot.state.ok.us/federal-grants/infra/2018/grady-county-us-81-realignment/application/ODOT%20INFRA%20Grant%20Application%20Grady%20County%20US-81%20Realignment.pdf (http://www.okladot.state.ok.us/federal-grants/infra/2018/grady-county-us-81-realignment/application/ODOT%20INFRA%20Grant%20Application%20Grady%20County%20US-81%20Realignment.pdf)
When comparing the proposed alignment with imagery in Google Earth it looks like the planners have chosen a path that's not very disruptive at all. They may have to buy and clear one or two properties between US-81 South of Chickasha and the spot where the old toll plaza on I-44 was located. North past the old toll plaza site the bypass alignment runs on mostly empty pasture land. I don't see them needing to buy any more than maybe a couple properties the rest of the way to the OK-9/US-81 junction.
The bigger trick is going to be getting the funding needed to build the highway.