Since this is the only area I have a reasonable amount of expertise I will do my best to provide an informative post:
Let me begin by making a few assumptions: I assume $3000 is not the limit but kind of the "range" you had in mind and that you also want a more timeless piece (i.e. nothing too far out there).
For this price point the obvious choices people will tell you are Omega, some IWC's, and perhaps Zenith. Depending on what you are looking for, my advice varies greatly. Your Oris watch is a decent choice for a first watch, although I wish you had given more information on the model or type so I could pick a second watch that would not be too similar.
To address your initial question: In my personal opinion, when I bought my first Rolex from a Brick and Mortar store, it was a very enjoyable experience. People were saying congratulations and one couldn't help but feel proud. The watch was sized there and I got to take everything home that day. Now, all that said, I have a relationship with this dealer now and have several friends that work there, if I did not, I would not hesitate to look online. From a "bang for your buck" perspective, online is the way to go. You can find the exact same watch that you will find at an AD (authorized dealer) and will likely save an additional 10-15% (depending on chosen brand). My final advice would be: if you are going to try and establish a relationship with an AD, then go ahead and buy from one. If you just want to get a great watch at a good price, buy online.
As for the watch suggestion itself: For $3k, I might honestly recommend buying online and/or pre-owned (i.e. used). My reasoning for this is that you can get a much higher quality watch if you look at the used market. For a brand new watch, $3k will probably get you a lower-tier omega, a lower-tier IWC (as has been stated), or maybe a nice Baume & Mercier. However, also for around $3k, you could score a used Rolex Explorer I, which in my opinion, is a very handsome and under-rated watch. The reason I suggest it, is that it is more versatile. A watch in stainless steel and with 100 M water resistance can be worn with a suit or with jeans and a t-shirt...and then swimming if you so desire. Another choice in the same vein as IWC is JLC, some of which can be found used at around that price point and is a spectacular brand (in my opinion). My personal favorite is the original JLC Master control. Basically my suggestion is to look around and compare new options to pre-owned, because once you buy it and wear it once, it is effectively "pre-owned" and no one will know the difference. That said, if you just want a nice dress watch, an IWC Portofino Automatic on a crocodile strap is not a bad choice. Why do I not suggest Omega? In my opinion, the original Speedmaster (moon watch) is the only model I truly feel is worth owning from them. There have been some reports of quality control issues with some of their movements, and they seem to make "limited edition" watches every 5 seconds. If someone has an Omega, I respect their choice, but I will not recommend them.
A little bit about movements: A great many watches use sourced movements from ETA. Common examples are the ETA 2824, ETA 2892-A2, and Valjoux 7750. The reason some people hassle IWC is that all of its watches do not use in house movements. For example, the Portofino (I believe) uses a modified ETA 2824. Breitling and Omega do similar things, although Breitling has recently come out with their B01/B1 and Omega has its co-axial technology. Granted each brand puts its own spin on these base movements, but at their core, they are ETA movements found in any Swatch. Depending on how much you care about movements vs. aesthetics, this may or may not matter to you. I should say that these are still tried and tested movements and have been around for a long time and you watch is likely at no greater risk of malfunction due to using an ETA variant. Servicing the watch may also be cheaper as most watch makers are familiar with ETA movements. From a prestige and collectors standpoint however, watches with in-house movements prefer to be favored. While I myself stand among them (hence my suggestions for some rolex models and JLC), I will not discount the credibility that ETA-based watches have earned. In the end, it is up to you, I simply felt you should be informed.
One word of warning, if you buy online, be careful. Request pictures and certificates of authenticity. Buy the seller first, the watch second. Also if it is an older piece, check when it was last serviced. Service costs can be around ~$500 for respected brands. If it has not been serviced recently, use this as a bargaining chip to bring the asking price down.
Look at JLC and some of the lesser known Rolex models
Certain Zenith and IWC models can be fine choices, maybe even a Glashutte Original
Buy the seller first, the watch second
Do not be afraid to buy online or used
I hope this was useful.