I don't think you are asking the wrong questions, but I also don't think you will get the answers you want.
"-I worked at a place for 4.5 years without a single raise."
Did this place have solid revenues? They very well may not have earned a penny, in which case the backers wouldn't necessarily OK a raise.
"-I worked at a place that blocked every port other than 80, and that blocked most websites that used post operations, all email websites, and all personal file transfer apps (like dropbox)."
Were you in a regulated company? (I know you said high-tech but even within that area there are companies bound by various regulations like HIPAA)
"-I worked at a place that literally did not allow working remotely"
See above
"-I worked at a place that only gave you three sick days per year. After that you were expected to either use your vacation days or accept unpaid days."
How many vacation days did they give you? I've seen some companies give more vacation days but force you to take vacation days when you are sick. All in all, I think I would prefer 4 weeks vacation and no sick days versus 2 weeks vacation and 2 weeks sick days.
"-I worked at a place that required 60 hours per week as a bare minimum, but in reality, expected more like 80+"
I'm reminded of the office space scene with the flair. Especially when you are joining an early-stage company, you should expect to work long hours initially (which should taper off as the business settles.
1. Yes, a solid revenue stream from previously released projects. The company had no problem spending money on frivolous shit.
2. No, it was a videogame company.
3. See above.
4. Two weeks, though in my case I was able to argue them to three because I had previously received three weeks at a different job.
5. It was not an early stage company, also it was a company with no proper goals or direction, and massive amounts of mismanagement. You weren't at work for 60-80 hours because you had a lot to do; you were there because they expected you to be there, whether you had work to do or not. Leaving 'early' was cause for shaming because of "letting down all the other hard workers".
edit: I am now working for a company that had answers to all the questions, and did not lie about them, and it is effectively a dream job. Part of asking questions is making sure you get answers, and if you don't, then bail.
"-I worked at a place for 4.5 years without a single raise."
Did this place have solid revenues? They very well may not have earned a penny, in which case the backers wouldn't necessarily OK a raise.
"-I worked at a place that blocked every port other than 80, and that blocked most websites that used post operations, all email websites, and all personal file transfer apps (like dropbox)."
Were you in a regulated company? (I know you said high-tech but even within that area there are companies bound by various regulations like HIPAA)
"-I worked at a place that literally did not allow working remotely"
See above
"-I worked at a place that only gave you three sick days per year. After that you were expected to either use your vacation days or accept unpaid days."
How many vacation days did they give you? I've seen some companies give more vacation days but force you to take vacation days when you are sick. All in all, I think I would prefer 4 weeks vacation and no sick days versus 2 weeks vacation and 2 weeks sick days.
"-I worked at a place that required 60 hours per week as a bare minimum, but in reality, expected more like 80+"
I'm reminded of the office space scene with the flair. Especially when you are joining an early-stage company, you should expect to work long hours initially (which should taper off as the business settles.