I do not like Davey's mother. I think it's very selfish of her to spend Davey's money like to so freely and let it slip to Davey's father so quickly that there's something he doesn't know about Davey and money and she did it all seemingly without a second thought. Davey may be her son but it doesn't mean she has the right to spend as much money as she did of his. She certainly doesn't know how much money he has or is making yet she's treating it like it's an endless supply. She could have spent all of his winnings and left him without a cent for important things - like College.
Davey is a very giving person and she obviously knows that. Davey seems at time to be too giving a person. The last two Do Overs he gave and he gave to his family and yeah he got his father's love, but how *real* was that? We know David can be a very cruel person to anyone that doesn't fit his beliefs - and Davey being gay certainly doesn't. Was Davey just away to get money and power and recognition? We know Davey's mom didn't think twice about throwing him away last Do Over, all she cared about then was that Davey got them nice furniture and clothes and things and then she threw him out and her relationship with him away when she learned something she didn't like. Sure her family was killed - and callously because Davey was a time traveller - but she had thrown him out before that happened. Will she do it again? She's certainly starting off in that direction, and quicker than the last time; at least, in the way of using Davey and his money to get herself better stuff.
Davey keeps trying to do the admiral thing and salvage/build a strong family for himself, but some things just can't be forced. He's trying to manipulate everyone into doing something that has proven to him on three separate occasions that it just might not be possible. And maybe he accepts that, but he seems to just be throwing this money around so willingly and letting himself being taken advantage of by those people who should never even conceive the thought of doing so.
Davey's Papa for all he's glad about Davey's "tips", seems to be being a better father for Davey than his real one and more caring too. And his Nanny, set in her ways she is, has proven she genuinely cares and will keep on caring for her family even after the do something that goes against her beliefs. She won't let it whatever it is she disapproves of be/happen around her but she wont cut the family member off - or for too long. They both seem like better parents than Davey's who both have proven on different occasions and different timelines that their love isn't unconditional.
And wow, that is long-winded. Oops.