I am mostly worried about long wait times and inexperienced support technicians.
That's a fair thing to be concerned about, and really only preventative way of running into such thing is doing a decent background check on the provider. See what others are saying about their support and level of experience and then take your chances from there. But other than that you should have a fair amount of options at a budget of $150 depending on what size Plesk you need. I think a Plesk unlimited for a dedicated server goes for about $30/month from the cheapest of third party license vendors too.
Any chance of finding a reliable hosting provider that can meet the above in under 150$/month ?
I have already done some research. It seems that Hostgator are in that price range but will I get the level of service I am expecting ?
Windows and Plesk would cost $50/month. Server management would cost at least $30/month.
So total left for server is $70/month.
It is not easy to find quality provider for your server and budget.
I'm surprised that HG can offer the server within your budget.
Even with fully managed server, support would not include script installation. Setup domain maybe but you should be able to add domain by yourself using control panel.
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A lot of providers can assist with setup but bill hourly. It's great if you want to lower your monthly price and need the bulk of the management done up front. Have you discussed paying for an initial setup by the hour so you might not need the monthly full management past your initial setup?
What type of a competent provider gives full management for $30/mo? I suppose it does depend on what the said provider constitutes as 'full management' and how proactive/detailed it is. As others have mentioned, consider getting Plesk for your Windows server so you can manage those aspects yourself. You won't get a good, truly managed Windows server for $150/mo. You can perhaps get something like a semi-managed setup where the company can give you a hand here and there.
Good luck with your search.
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