Worst WTF dev experience? The login process from hell to a well-fortified dev environment at a client's site.
I assume a noob admin found a list of security tips and just went like "all of the above!".

You boot a Linux VM, necessary to connect to their VPN. Why necessary? Because 1) their VPN is so restrictive it has no internet access 2) the VPN connection prevents *your local PC* from accessing the internet as well. Coworkers have been seen bringing in their private laptops just to be able to google stuff.
So you connect via Cisco AnyConnect proprietary bullshit. A standard VPN client won't work. Their system sends you a one-time key via SMS as your password.

Once on their VPN, you start a remote desktop session to their internal "hopping server", which is a Windows server. After logging in with your Windows user credentials, you start a Windows Remote Desktop session *on that hopping server* to *another* Windows server, where you login with yet another set of Windows user credentials. For all these logins you have 30 seconds, otherwise back to step 1.
On that server you open a browser to access their JIRA, GitLab, etc or SSH into the actual dev machines - which AGAIN need yet another set of credentials.

So in total: VM -> VPN + RDP inside VM -> RDP #2 -> Browser/SSH/... -> Final system to work on
Input lag of one to multiple seconds. It was fucking unusable.

Now, the servers were very disconnect-happy to prevent anything "fishy" going on. Sitting at my desk at my company, connected to my company's wifi, was apparently fishy enough to kick me out every 5 to 20 minutes. And that meant starting from step 1 inside the VM again. So, never forget to plugin your network cable.

There's a special place in hell for this admin. And if there isn't, I'll PERSONALLY make the devil create one. Even now that I'm not even working on this any more.

This is a part rant-part question.
So a little backstory first:
I work in a small company (5 including me) which is mostly into consultation (we have many tech partners where we either resell their products or if there is a requirement from one of our clients, we get our partners to develop it for them and fulfill the client requirements) so as you can see there is a lot of external dependencies. I act as a one-hat-fits-all tech guy, handling the company websites, social media channels, technical documentation, tech support, quicks POCs (so anything to do with anything technical, I handle them). I am a bit fed up now, since the CEO expects me to do some absurd shit (and sometimes micro manages me, like WTF I am the only one who works there with 100% commitment) and expects me to deliver them by yesterday.

So anyway long story short, our CEO finally had the brains to understand that we should start having our own product (which i had been subtly suggesting him to do for a while now!).

Now he came up with a fairly workable concept that would have good market reach (i atleast give him credits for that) and he wanted me to suggest the best way to move forward (from a both business and technical point of view). The concept is to have an auction-based platform for users to buy everyday products.

I suggested we build a web app as opposed to a mobile one (which is obvious, since i didnt want to develop a seperate website and a mobile app, and anyway just because we can doesnt mean we have to make a mobile app for everything), and recommended the Node/react based JS tech stack to build it.

At first he wanted me to single handedly build the whole platform within a month, I almost flipped (but me being me) then somehow calmed down and finally was able to explain him how complicated it was to single-handedly build a platform of such complexity (especially given my limited experience; did I mention that this is my first job and I am still in college, yeah!!) and convinced him to get an experienced back-end dev and another dev to help me with it.

Now comes the problem, I was to prepare a scope document outlining all the business and technical requirements of the project along with a tentative cost, which was fairly straightforward. I am currently stuck at deciding the server requirements and the system architecture for the proposed solution (I am thinking of either going with AWS - which looks a bit complicated to setup - or go with either Digital Ocean or Heroku):

I have assumed that at peak times we would have around 500-1000 users concurrently

And a daily userbase of 1000 users (atleast for the first few months of the platform running)

What would be the best way forward guys?

I did some extensive (i mean i read through some medium blogs! and aws documentation) research and put together the following specs (if we are going through AWS):

One AWS t3.medium ec2 instance for the node server (two if we want High Availability by coupling with the AWS load balancer and Elastic Beanstalk)

The db.t3.small postgres database

The S3 Storage bucket (100gb) for the React Front end hosting

AWS SNS for email/sms OTP and notification

And AWS CloudMonitor for logging amd monitoring.

Am I speculating the requirements properly, where have I missed??

Can u guys suggest what is the best specification for such a requirement (how do you guys decide what plan to go with)?

Any suggestions, corrections, advices are welcome

Compare and harmonize the web configs

Oh no someone set execution timeouts to 14 days

Fuck fuck fuckity duck

Hey compare all the web configs of all environments and harmonize them all wtf cmon bruh do your job as a developer

Take them and back them up into svn. What do you mean svn isn't a back up system of course it is well its the only thing we have fuck

What do you mean we have shit logging where people will catch an exception and only print the word exception in the log you can figure it out can't you we have live produxtion issues that hace to be solved now what the fuck

How dare you make a. Mistake copying our shitload of a bloated codebase and configuring our 100s of different options all by fukcing hand what the fuck dude do yoh write anyrhing down?

Please catalogue all the exception mails we are getting but we have no db or error reporting system so they all just plop into tue inbox and thats all ypur fuckjng data figure it out kid

This is a rewarding, fulfilling job whwrw you can be both dev ops and a developer and manage all of our fucking environments of which there are about 15 of all your own with no sort of tool or software to aid you because haha what the fuck we wouldn't make your life easy

Whata that you want to spend time to write stuff or change stuff that will nake it easier fot you fuxk that bruh get back to your biklable tasks like holy shit you thjnk this is a charity ofr aomw shit

Live production issues
Live production issues
Produxtion issues. A ghost in the machine. Find it fix if find it fix it find it fix it cmon why can't you fix it I expect you to spend your day hopelessly pretending to try to solve something you fucker

One of the only peopel able to help you sometimes though hes a bit of an old laxky, yeah hea fucking leaving see ya seeya kid and now we're not hirinf anyone to fuckjng help you no no no managing and monitoring the environments its your jov alll fof them every sngle on do you knkw all the xonfiguraiton values for them yet??

Instead we are hiring a new sales person to fucking make us some more money and we don't need naother seceloper to help you infqct lets have you use this mid end retail computer from 2014 to develop on yeah yeah oh but all our shitty code and visual studip will destry your memory but too bad!! Hahahahahdhsj

Go lice is all you, why sare you so slow

How long will it take
How long will it take
How long will it take
How long witll it tqk2
How long will it take holy shit
Give time estimate for sonethign that I don't fucking know how about it will tqke till fuxk you oxloxk