my generator sets about 150 feet behind the house, in a shed I built for it, I ran a conduit under ground and ran aluminum service wire, back to the transfer switch, and there is also a wires running back to the shed for the power in the shed, and to power the well which is near,
some times all you can do is spend some money to do it correctly,
I prefer a manual transfer switch, I have nothing that is such that need power 24/7, and generators are expensive to run, can be very expensive, the larger ones can go through 2 to 5 gallons of fuel an hour depending on loads,
So if we or need to use the generator, I will start it and run for the need, it is large enough for keeping the well and freezers and refrigerators, going for some recharge time, and then shut off, for until a real need is needed,
I my self would not go to an automatic switch and auto start unless there was medical equipment or some other need that needed a constant supply of power,
a few led camping lanterns will provide light for pennies.