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Ideally if you are to run cat5/6e to the geust house it should be done inside a buried pipe or else it will go bad from exposure.
There is zero connections from the main house to the guest?
Its not worth the cost to get another service installed imo running the wire will be a higher inital cost but will resolve any other headaches in the future when it comes to providing service there.
Distance is your biggest issue here, with the current location of the modem you have little chance of providing solid service to the guest house with repeater or extenders in my opinion. You could always wire a cat5e to a backroom than run an extender from there to get service tho I doubt
how good it will be unless you buy some really nice gear. Apples new ac wireless router is amazing for strenght and distance but cost a shit ton
Horizons is a cabling company tho I have seen pretty mix work from them so it will depend on the actually installer.
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