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My home LAN consists of a D-Link DIR-885L Router (Wired and WiFi 802.11ac), a D-Link DAP-1560 Wireless AC1200 Dual Band Gigabit Range Extender (in 5gig Bridged Mode), a 4 port switch, 4 Windows PCs, iPad. iPhone, Samsung TV, a Channel Master DVR, and an HP Wireless Printer (iPad, iPhone, and the printer are always used via WiFi).

Because it would be a pain in the neck to get Cat Cable to the other half of the house I have the DAP-1560 (as a wireless 5Gig bridge) in the Livingroom with the router (across the room, line of site, with no walls or other obstructions) and then a patch cable through a wall behind my TV to a small 4 port switch and the two PCs, the TV, and the DVR on the other side of the wall are connected via Cat cable to the switch.

Question 1: Is there a better device or configuration (using the devices I have) to connect my LAN. I have tried placing the bridge on the other side of the wall but the 5gig signal level drops noticeably with just that wall as an obstruction.

Question 2: I'm using dynamic ip addressing (with the exception of the Bridge and the printer) with the router acting as the DHCP server for ip addressing to all the other devices. Should I just bite the bullet and manually use static ip addresses for all the devices?

Question 3: Despite the Router issuing the dynamic ip addresses to all the devices it displays/confuses/combines the bridge and the devices attached to it in its client list (doesn't show them all or their ip addresses, but sees the bridge yet shows one of the down stream devices ip address). Is there a way to resolve this?

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Question 1: Is there a better device or configuration (using the devices I have) to connect my LAN. I have tried placing the bridge on the other side of the wall but the 5gig signal level drops noticeably with just that wall as an obstruction.

Depending on your home wiring, power-line communications (e.g. HomePlug AV standard) can work better than Wi-Fi. (Although the actual link quality can vary greatly, and both ends need to be on the same electrical circuit.)

If there are very few 2.4 GHz Wi-Fi networks around, it would be possible to use a 2.4 GHz bridge – 802.11n in 40 MHz mode might reach up to ~100 Mbps.

Question 2: I'm using dynamic ip addressing (with the exception of the Bridge and the printer) with the router acting as the DHCP server for ip addressing to all the other devices. Should I just bite the bullet and manually use static ip addresses for all the devices?

That's not necessary in your case (in fact it doesn't seem to be related to the other parts of your post at all).

Question 3: Despite the Router issuing the dynamic ip addresses to all the devices it displays/confuses/combines the bridge and the devices attached to it in its client list (doesn't show them all or their ip addresses, but sees the bridge yet shows one of the down stream devices ip address). Is there a way to resolve this?

It slightly depends on how the router builds its "client list".

In order to fully preserve the devices' MAC addresses in the Ethernet header, Wi-Fi bridges need to run in a special "WDS" or "4addr" mode – as normal Wi-Fi assumes that each wireless client has only one MAC address (its own).

Not all Wi-Fi "range extenders" support this mode (and it needs to be supported on both sides of the link; the AP and the client). Most of them simply run in regular 3-address mode to remain compatible with standard clients or APs, and the bridge acting as "client" has to transparently rewrite all MAC addresses going through it.

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