Planet86

What OS are you running? If its Linux or BSD based just run ZFS. Don't bother with a hardware raid card.

Moving to iocage you will be able to update the base of the jails. There is supposed to be a tool to transfer warden to iocage.

Plugins are switching to iocage jails and will be much simpler once they release 11.2 which is coming in a few months. Bhyve and docker are already there but you will still get the best performance running jails. What issues have you had using Plex in a jail? It's super simple to setup as long as you have the correct permissions.

Dont worry about ignorant, I know the HP board looks like a good deal but you're going to have way more headaches than it is worth. Even if you buy the right PSU and cooler it still won't work and you're going to end up spending a lot more money to get it to work. Take a look at the fully assembled system that the board is meant for. You could probably buy a full DL380 G6 server ready to go for a couple hundred bucks. Here are dual socket Xeon boards form SuperMicro: https://www.supermicro.com.tw/products/motherboard/Xeon1333/#1366

As I mentioned before it uses all proprietary parts only designed for a DL380 G6 server. 1366 Cooler: No this board does not use standard mounting holes for 1366 PSU: That is the correct PSU however it wont work unless you get the DL380 G6 case/cables. Case: This will not fit into any standard case other then the one it was designed for. You'd have to build your own case for it. If you're not running anything intensive just build it with a newer desktop CPU and motherboard. You don't need a Xeon to support virtual machines.

This is a board meant for a rack mount server, it uses a proprietary cooler, psu and case. You will most likely not be able to make it work without buying all original HP parts which will cost you alot of $$$ individually. You could probably pick up a DL380 Generation 6 (which is where this board is from) pretty cheap. TLDR: That system is also going to draw quite a lot of power, I would try to go with a newer 6-8 core CPU. If you really want a dual socket board Supermicro makes some that will fit into a ATX or EATX case and use a standard ATX power supply.

You can run Hyper-V since you have Windows 10 Pro. You will definitely want to upgrade your memory though.

Skip the drobo, unless you don't care about losing your data. How old are your externals? If they are approaching 3 years its probably best to just buy all new drives for your NAS.

Are you able to access your dataset within your jail?