Before you say you know what I have not thought of, I have been involved in the seasteading community for almost a decade.
We will have a seastead, we have a path forward. It will happen.
Everything you listed has been addressed long ago (other than the every woman being crazy thing).
I'm not saying you can't get on a boat, I'm saying it might be difficult to have what most people consider a normal life there and even if you can you'll probably end up paying more for it than otherwise needed.
If you have a solution to all those things I wouldn't mind hearing them or seeing links. If you just really really want to wish away the problems and daydream I'll leave you to it.
Ok, while many solutions are discussed ad nauseum among seasteaders and no one solution is the best I will address what you listed:
Maintenance - Boats rust, even glasfiber boats need to be taken up once a year and painted etc..
We're not talking about a boat here, we're talking about platforms (around 50 to 100 meters wide) that can interlock and expand to a city sized seastead.
The popular consensus has been that it should be built out of concrete. This will last hundreds if not thousands of years. One of our experts has built similar structures and there are many working examples of floating concrete platforms (one even has a landing strip on it).
Cost - Land is pretty cheap even in urban areas compared to a boat. Large boats costs millions. Remote areas of land where you could do whatever can be gotten for very little.
Cost is certainly a factor. You could buy something in middle of the US but the first million dollars that your community brings in will get the attention of the government.
Our initial estimates on cost using concrete are fairly comparable to oceanfront real estate. As the platform can float and be located anywhere we are looking at affluent harbors where real estate prices are in the millions. That makes our housing options very competitive giving a good return on investment.
Jobs - What will people do? Even if we assume that our liberal ideas would create a 100 times better economy its pretty hard building an economy with 20 people on a boat/remote island.
The seastead will be far more than 20 people. The investment group has planned to build at least 6 businesses into the initial structure with one business actually being the building of more seasteads. It will likely be a tourist destination which will provide plenty of monetary inflow.
Supplies - Remote as you are almost everything will have to be flown or shipped out to you adding even more cost/making you need a second ship/plane.
The initial seastead will not be remote. But we have certainly discussed such a thing down the line. The seastead community will need to be large enough to warrant such a move which comes with several costs such as breakwaters, mooring and several other factors including establishing a trade route. The popular opinion being that we should position it within an established trade route and take advantage of that as a hub.
Seasickness.
Waves and saltwater are the constant issue being addressed when it comes to engineering. Like I said, the initial one will be in a harbor because we will be focusing first on engineering and a viable business model. Breakwaters and designs to minimize wave impact are a constant discussion.
How to get to the doctor.
It is our hope that a medical facility will be one of the main businesses providing medical tourism. People are willing to fly to foreign countries for lower cost medical treatments due to a lot less red tape and more freedom. Medical advances will likely thrive on a seastead.
Entertainment in a small area.
Entertainment will be abundant. Swimming, fishing, SCUBA, nightclubs, concerts, boating, jet skis, you name it.
All the politics - Anarchy hur hur is great and all, but who decides where the boat goes or what to invest in. What is the political framework for dealing with a guy raping his daughter or is that fine? I'm guess there's a thing or two there you haven't considered in your dreams of blue waters and escaping the state.
There will likely be different political structures for each seastead. Initially we will be under the laws of whichever nation we fly our flag under and whichever nation's harbor we are docked in will have limited jurisdiction, there are many legal issues that have been discussed when it comes to nation laws and distance from land. When it comes to seasteads outside of the EEZ, each seastead will have to come up with the societal structure that they like best. And with multiple of these, we can essentially have government startups. Some will succeed, others will fail. When you can float your house away to another seastead, there will be competition to keep people.
Guns you need guns for pirates.
While we will not be settling in in heavily pirate populated areas, there will be no shortage of guns owned by seasteaders.
Internet - You won't have it that far out, not fast anyway. Wifi bridges can shoot 20km if you're static at the coast, but it's something to consider.
Just like with trade routes, ideally we would set up in a place where we can become an Internet hub with underwater cables. As most telecom people can tell you. It is not the cost of the fiber that is expensive but the cost of laying the cable (government fees, regulations, lobbying, etc). There can also be satellite which is more expensive and not good for real time streaming but will be good for redundancy. In a harbor we will likely do a microwave type of setup, wifi and underwater cable.
Power - How do you make it? You can't afford something big and efficient/the boat can't hold it so you would have to use a diesel generator and solar panels and shop each month for expensive fuel.
Power will be abundant with the power of the sea. OTEC (Ocean Thermal Energy Conversion), wind, wave power, solar, hydrogen producing algae, etc. Many people suggest selling electricity to the host nation but I think we could use any excess electricity for cheap mining operations.
Also solar panels break/degrade after 10-20 years and give relatively little power in the meantime.
Yes, solar panels are usually rated for 20 years. It would be unwise to pay for anything that does not give a return on the investment over its lifetime. But the price has come down quite a bit on those.
Housing - Can you build a house? Plumbing? Wires? Insulation? AC?
Housing will likely not be your typical square house with slanted roof. Most likely dome shaped or containerized housing units (CHUs, which they use in Iraq/Afghanistan) or some other design. OTEC provides fresh water and air conditioning as a bi-product, using the cool water from lower depths will make housing very comfortable.
Like I said, there are many solutions so the ones I listed are just cherry picking from several discussions. We have the expertise and our builder does not see any issues in getting the initial platform built once the design is in place and the investment is finalized. That is what we are working on now.
I am dedicated to making this happen. I have already left the US and have downsized my lifestyle so that I can pick up and go at any moment. I will definitely be one of the first ones living on the seastead so I have made sure to have my input when it comes to design so that it will be a liveable environment with everything for daily living addressed.