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Sometimes, I wonder.
I just don't know
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If it is serious stuff, you might want to hire someone skilled in the art. You could ask for recommendations here.
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If it is to sell inventory, rather you could do proper research and get something done on the cloud using azure or aws (or look for a it solution provider to do it for your company). There are eCommerce solutions you could deploy onto the cloud.Considering that what ever you make should be secure enough and properly tested.
Caveat Emptor.
"Progress doesn't come from early risers – progress is made by lazy men looking for easier ways to do things." Lazarus Long
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Just one initial alarm bell (out of several) that rang for me - I was working a year or so ago with a client who was running Server2008; that OS doesn't support TLS1.2 and as a result, very few browsers can talk to his server any more over HTTPS. Support for TLS1.0 (and 1.1?) was pulled from Chrome, for instance, many months ago. At the same time browsers, and AV systems etc, are flagging sites that don't support HTTPS so his clients (businesses, not even the general public) couldn't reach his site. For various reasons I won't go into here, the client couldn't upgrade. A workaround I made clear was a short-term kludge was to point his domain at one of my servers, and run a proxy server on that using plain HTTP to his aging server. Clients happy, communications restored. (Needless to say, it's still up and running now and no news on any move away from that setup).
In summary, you may find that Windows Server 2008 is not a viable system to run a website on in 2021.
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To what extent do you think you'll update the site?
I recently went through a similar process updating a 2003 website to current standards and also developed an API version, all with VB.
I started with a hosted VM then went to a dedicated server, keeping the VM for development.
I bought books on VB in ASP.Net 4.5 but found that they weren't as basic as I needed them to be - it was easier to use my old books on v2.0 and v3.5 to get started and then move on as I developed new features, finally swapping to an API basis for the most advanced versions of the site.
I would recommend you get VS2019 as a start - is there any reason why you can't move from VS2015?
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I think you and I are very similar. We're the multitaskers that can "hack" something together to make it work. As you can see from the other replies, there's a lot of variables that go into an external facing e-commerce website. If you're not on top of them, it could be disastrous to say the least. Maybe someone could recommend a skinnable e-commerce service in the cloud or something prepackaged to minimize your risk.
Disclaimer: I apologize if I've read too far into your question.
modified 21-Dec-20 8:50am.
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I would first say to my self "what are we actually trying to accomplish?" A lot had changed in 7 years and there may be other ways to get the job done. For example I have a client that had a full e-commerce site that switched to etsy, her sales have only gone up.
I would suspect your SQL Server tables and procedures etc should be just fine on new hardware.
For all the excitement of the past 10 years the basics of web development are still the same. POST and GET still do the same things. works the same.
What do these programs do? Who will be using them? A few internal users or public website?
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I would consider converting Ecom to something like Shopify, etc. With security, ssl transactions and other at your age(like me) I’d let someone else carry that load.
I’d continue company VB programs with 2015. Not a lot has changed with DB hookups. You can solve most questions/problems with stack overflow.
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I'm an old guy, too. One thing I've learned is to throw away my books. Every framework or language has tutorials on the web. That's where I would start.
My most recent preference is ASP.NET MVC in C# with Entity Framework 4.8. I would recommend Core, but it is subject to so many frequent, breaking changes, and there is no Microsoft Reporting Services version that supports RDLC under Core, yet.
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If you buy a bigger bed, you have more bedroom, but less bedroom.
Wrong is evil and must be defeated. - Jeff Ello
Never stop dreaming - Freddie Kruger
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Bed set theory.
It was only in wine that he laid down no limit for himself, but he did not allow himself to be confused by it.
― Confucian Analects: Rules of Confucius about his food
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This gets even more interesting when you add one or more greyhounds to the formula. More bed means fewer dogs on the floor, which means more floor space which is taken up by the bed. Less floor space means less room for you to sleep (you didn't think you slept on the bed, did you?).
[testimony from the owner of two retired racers]
Software Zen: delete this;
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And then, letting someone else run with your basket: Solarwinds.
Public company, government systems, foreign money. What could go wrong? 
It was only in wine that he laid down no limit for himself, but he did not allow himself to be confused by it.
― Confucian Analects: Rules of Confucius about his food
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So what you’re saying is that there is no reason whatsoever to worry about the voting systems in the US election. Got it!
If you can't laugh at yourself - ask me and I will do it for you.
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You're confusing spying with altering records. But, "they" could try your logic ...
It was only in wine that he laid down no limit for himself, but he did not allow himself to be confused by it.
― Confucian Analects: Rules of Confucius about his food
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I used the expression "Incompatibility Matrix" in one of my documents ...
... and of course, because of my bad english I tried to cross check that on Google Translate.
But Google Translate insists that "Incompatibility" is wrong and only accepts "Compatibility".
Where I'm wrong?
Thank you in advance 
And while I'm cross checking the above with google, no issues 
Seems to be solved, anyway hints still welcome, thanks.
It does not solve my Problem, but it answers my question
Chemists have exactly one rule: there are only exceptions
modified 19-Jan-21 21:04pm.
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Thank you very much.
It does not solve my Problem, but it answers my question
Chemists have exactly one rule: there are only exceptions
modified 19-Jan-21 21:04pm.
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As with a spell-checker that doesn't recognize all words, or all forms of all words, so it is with Google lookup. That you found "Comparability Matrix" should reassure you about the expression (assuming your desired incompatibility definition is in line with the given meaning, except for the negation).
| Ravings en masse^ |
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| "The difference between genius and stupidity is that genius has its limits." - Albert Einstein | | "If you are searching for perfection in others, then you seek disappointment. If you seek perfection in yourself, then you will find failure." - Balboos HaGadol Mar 2010 |
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Thank you very much.
It does not solve my Problem, but it answers my question
Chemists have exactly one rule: there are only exceptions
modified 19-Jan-21 21:04pm.
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I am English from England and speak both English and American fluently.
"Incompatibility" is a perfectly good word. Google Translate is not a comprehensive dictionary of English, but does it's best. However, just because it doesn't know a word or a particular variation of a word, "Compatible" in this case, doesn't mean it is correct and you are not.
- I would love to change the world, but they won’t give me the source code.
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Thank you very much.
It does not solve my Problem, but it answers my question
Chemists have exactly one rule: there are only exceptions
modified 19-Jan-21 21:04pm.
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Don't get me started... 
But, no, you're correct in this particular instance.
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