re: New (2) Desktop Computers by Dell - What's the Best For My Needs?

Get a 2 or 4 bay NAS, load them up with some good 2tb drives. thats anywhere from $300-800. leaves a lot of room for your desktops. like someone else said the XPS's are good to start. with that budget, get i7 8th gens, lots of ram and 256 or 512 SSD, and a Graphics card

Dell XPS

i think intel has paid dell and hp to both push their shitty optane solution over giving a proper SSD option in their builds.

i swear i fricking hate the hardware industry

You don't need a server for two people.

Get 1 Office 365 Premium Subscription ($12.50/month).
- Gives you the desktop version of Office for 5 PCs.
- Gives you a 1TB cloud drive for file sharing.
- Gives you one email and a contacts/calendaring solution.

Get 1 Exchange Online subscription ($4/month) for the second email.

Quickbooks online is between $10-30/month depending on the version you need.

The Optiplex is Dell's business desktop line. The configuration you get really depends on your software requirements. An i5 w/ 8GB RAM and a 128GB SSD is suitable for most office needs.

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My Desktop Computer is a Dell XPS (Core i5)

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Core i5 is the naming convention for 8 generations of CPUs. Just saying "i5" is like saying, "I drive a mustang. How old is my car?"

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Server is a Dell PowerEdge 110 

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Sort of as above. Poweredge is a set of hardwares. It varies from Celeron to xeon processors, RAM with different speeds and capacities, hard drives...not unlike
"are mustangs fast cars with big engines?"
Well, v8 5.0L are. But they also have 4-cyllinders. We have to have more information for the answer given to be useful.

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Programs: Microsoft Office - that's really about it. I get most of my content from websites (plans, specs, etc.) 

Though we have our own domain for emails, it's funneled through gmail. Not sure how much space we have, but I never delete emails. 

Budget is going to be $5,000 for the following... 

(2) Desktops 
(4) Screens 
(1) Server 

If I have left over money to spend - it'll be on printer & scanner

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What exactly do you want/need a server for? Would a NAS do the trick for filesharing and backups if you're not hosting anything?