Congrats @Chris Bluem! Here are some quick answers from my perspective/experience, answers will likely vary on these depending on market, business model, available resources, etc.
1. I have created automations for rental agreements for many friends/clients, however I personally have never used one myself and simply rely on the agreements and amendments I have added to the listing sites. So, it's sort of up to you I think...it adds a layer of complexity to the process but provides additional confirmation that the guests understand your rules. Whether or not it actually provides more legal recourse then the listings agreements, I don't really know...I doubt it though.
2. Looks pretty standard, below is a outline of a common one I have built in the past, which you can take some or all of those to incorporate depending on your situation.
3. I assume you mean the list of things the cleaners need to do when the clean? You can have all the lists you want, the cleaners are going to come in and do their thing though unless you have one that is willing to actually check everything off...even if they do, they might just 'check stuff off' and clean how they will. In the end, it's going to be about how your guests respond to the property when they check in. No complaints, then they are doing well but if more then a few complaints come in, I would start looking elsewhere.
4. Lots of people do this and I think it has value, I personally never did just because I liked a simple 2 day minimum across the board. There are other rules though that you might want to prevent a weekend from getting blocked off because of a weekday stay bleeding in. Once again, more complex than I cared to get into it, but certainly valuable if you have the means to setup.
Best of luck!