I've been crewing for a bit now and I think I want to get something lower-risk to start next reason before I can commit to a 50-100K boat.

I was thinking a Pearson 30 or Tartan 34C, there are a lot of owners going into retirement and want to offload their boats way below value.

However, I understand things like engine, rudder, hull, and wiring can be checked. Mooring and marine and storage can be solved with money (I'd budget about $4K/year for those).

I wonder for those who have done the same, what are something you would do differently if you are to do it again?

The boat is an 11 m steel sailboat, currently on the hard. The windows it seems arent mounted directly to the steel hull, which i found out when investigating a leak. There's a piece of wood between the frame and the hull, and it seems the wood didnt rot but is leaking between the wood and steel, the window also seems to be sealing ok.
Photos attached.

A few questions:
Should I take the window out and reseal everything, or is it better to just replace it while it’s out anyway?
When I remount it, should I go back to a wood spacer, or mount it directly to the hull? If wood is a bad idea, what do you use as an isolator? G10, HDPE, just a thick bed of sealant?
Any recommendations for sealant, fastener isolation and how to prep the steel underneath before it goes back on?
Thanks in advance, any advice is appreciated!