Genera advice on buying a boat (35-50ft) less than 10 yr old, Chicago

[gold871101]

Hello all, I am new to this forum and need help on purchasing a boat.
General back ground, we live in Chicago , IL, knew about boating last year from our friend who own a Sea Ray 330 early 2000 model, we liked it so this year we purchased boat membership for 2009 FourWinn 378 , we just finished water training and very excited to boating our self. Boat membership is great but does not allow overnight staying which make us consider purchase our own.
Due to my work, there is possibility i might need to relocate in 3-4 years, lets say 50% chance, so I dont want to get heavy hit with new boat depreciation.

I search near illinois and found several potential buying.
We could consider up to 700-800k but prefer to stay under/around 500k due to relocation possibility.

We are young couple with 2 year old, will just enjoy with three of us until COVID thing become less concern. Playpen, dock hopping stay as cabin, cruise river.

Heard Sea Ray is good since it is locally made and easy to maintain/ sell.

Some list we consider with some search. Ones with * is most likely potential.
55 Prestige 2013 750k
54 Sea Ray 2011 700k
44 Beneteau 2015 400k*
44 Beneteau 2013 370k*
42 Regal 2014 440k*
41 Cruisers 2013 400k*
40 Regal 2008 190k
37 Formula 2012 230k
35 Monterey 2017 250k

Any general advice would be very appreciate!

Thanks