It depends on the cables. Granted, I have 1m cables, but I detect no signal loss between being on the pigtails and being directly connected to my router. Less than 1dBi of signal loss.
It depends on the cabling. If it is "low loss", it is likely an LMR-400 cable, which is 6.5dBi per 100ft.
What you are proposing should be fine...but depending on the spread, a single centrally located wifi router, even with large antennas may not work to get signal to the further structures, especially if they are a block construction and not stick construction.
My garage access point as its pair of 5dBi omni antennas on the ends of 1m pigtails sticking through the wall of my garage directly under the eves of the roof there. I get nice signal over my entire backyard (1.01 acre total yard), but step in my shed at the furthest point away, about 100ft, with the door closed and it is a bit border line. Still fine...but its around -70dBi, which is getting down there. Step behind the shed so both walls are between you and the access point antennas as well as another 10ft and its down to about -74dBi.
I think if you are going to get it to work, you are going to use some VERY substantial antennas, like 12dBi or even 15dBi outdoor rated antennas. Ideally you'll want the AP as close to the antennas as you can to reduce signal losses over the cable.
In the end, what I think you'll need to look at doing is several access points over the property to cover everything. Either connect them up with Cat5/5e, outdoor rated and bury it, or else you MIGHT be able to get away with some powerful wifi range extenders, though you'll be compromising the wifi throughput by doing this.
Another option if you want to do it all wirelessly is wireless bridges and then access points connected to these bridges. Depending on line-of-site, frequencies choosen, etc it should be fine if you stick with the bridges on 5GHz and the guest network on 2.4GHz. You could have 3 bridges/APs located around the periphery and a central AP connected up to 3 bridges to hit up the peripheral ones. Then set the 2.4GHz channels so that they are not physically overlapping and Bob's your uncle.
Well, after LOTS of tuning.