We are looking into a hand pump on a second well, and most of us have thought out your 5 points, most are aware, how ready everyone is I have my doubts...
A Second Well? Round here that is a 20K hole and it might come up dry- even 20 ft from a working hole. This can probably share the current well casing -
http://www.simplepump.com/OUR-PUMPS/Hand-Operated.html - It also isn't cheap, but way cheaper than a second well.
I have a buddy having the same issues with his family - which include an Aunt he deeply loves, who is marrying a useless drunk, a step-father whose plan is to die before SHTF, and his mother who is for the most part on-board, but paralyzed by doubt and the reluctance of other family members. His parents have a huge Ranch with a river a mile away - plentiful game, good farming and pasture. - but they aren't doing anything to prep it. He started on his own with a smaller place and went in with his Aunt, but the Drunk is F'ing up that situation so bad he is ready to bail on it and start over.
I have a doctor in my group - he bought a place near mine, but has done nothing ( 0, nada, zip- not even spent the weekend) since.
Not taking it seriously- for sure.
Of course, my immediate family, being liberal , is out of the picture from the get go- and the more I learn the more it seems a blessing. I am trying to get this buddy to throw in with us - but it means "giving up" on his family and he understandably isn't ready to "go there" yet. ( I told them we can plan to have them join him.. but Colo isn't "home") Bottom line, the best people to prep with may not be your family - or at least not all of it. No one wants to admit it, but triage is a process that is and must be on the table. As I said to CO, dying for Love isn't the best plan. None of us are ready, and won't be till after the event occurs - because there are so many unknowns in how this will go down. I am a cold, logical heartless bastard. I just do the math. Conservatives are supposed to concentrate on the unpleasant things in images- well I do that in spades. I may not be happy, but my eyes are open. Our society has created a number of individuals who just won't (can't) accept that tough choices are going to have to be made, and if you wait for them to "come around" you will be waiting literally until doomsday.
You need to get the willing people into the room, discuss what scenarios you are planning for (we are not prepping for an EMP for instance), what you are leaving to chance, and what the plan is, what priorities are, and then you can then decide how to pay for it. Write it all down - family or no, writing keeps things from "changing" --at least without agreement. If its $50 a month from each person, then that is what it is and you proceed as quickly as you can at that pace- you may even want to make this part of your C-Corporation... If someone "comes around" and wants to join the pact- that is another $50 a month and maybe a late joiner fee- but the plan don't change. They are lucky that you are allowing them to "join" - stipulate shares and specify how things will be liquidated if the partnership breaks up, and under what circumstances that can be - ( an individual leaving gets nothing) a vote of half of the members results in liquidation - or whatever. It won't prevent problems, but at least there is an agreed to method of dealing with them.
Ideally you have both a Gen AND a PV system. If the group decides that the Gen comes first (and it probably should, because a 7 day outage is way more likely than a 2 year outage) - then it comes first - but that purchase is made with an eye to the long term plan- i.e. supplementing a PV system in a long term situation - and that probably DOES NOT mean gas. Diesel or Propane, and only enough to run the Absolute minimum people are willing to accept.