Hi Hill Billy, and welcome to CF. Sounds like you have some challenges ahead, especially looking for a $5k boat. They are out there but most are pretty spartan, and it sounds like your partner is looking for some creature comforts. A decent
shower means at least about 35'.
WiFi come with a lot of
marinas now but if you are looking at the $500/month lifestyle you won't be staying in
marinas. Not sure what you mean by "put in the graft" to get her
seaworthy, but it will take some $$ for upgrades and
equipment not just labor.
Hopefully, you can get "her" on board 100% because it will take a team effort to make this
work. Don't know your ages but I'm guessing you aren't
kids that don't mind living the minimalist lifestyle. Anyway, good luck and let us know how we can help.