Welcome to Trawler Forum.
In my own experience various things appeal to various people. Before I took up cruising/liveaboard life I had all the bells and whistles, successful business, trophy wife, members of institutions, lodges etc and do you know what ?
When you decide to rid yourself of all the paraphernalia of land its amazing how free you can be after the solicitors have raped you.
Yes there's lots of memories, but that's all they are, memories !
I brought one small suitcase when I moved on board, some mementoes, family bible, army citations, medals, offered the rest to the family and dumped what was left.
I started another business while based on board and its happily paying me to cruise around the South of France and travel. Read my post 'Traditions and Travel'
Don't plan too much for visitors, use the space for your daily living and let them 'bunk up' when they visit because they won't come as often as you think they will when the novelty's worn off.
In my honest opinion buying a wooden boat is worse than a bad marriage, none give you peace,both have to go in the end, the only difference is time.
I fully agree with Old Dan that paper charts are a brilliant way to orientate your brain to coastal cruising or passage making, you maybe don't believe me but your brain will accept and imprint a chart, whereas it will forget a screen shot.
At the expense of being called a boring old fart I still use charts to plot with compass & pencil, I only use a simple Garmin GPS 72 unit because its easier to read than a swinging compass.
My sometime cruising mate has the latest all singing all dancing Garmin, according to it we've been cruising fields, its taken us up a blind alley on canals and once put him 5 miles of a river entrance, apart from that its fine.
Health ? You'll find that with the stress gone and doing what you enjoy with a healthy lifestyle will increase your lifespan.
Just one word of caution, as you and your good lady will be in close proximity 24/7 its probably the number 1 reason for boat sales after health.
Measure twice, cut once, have faith and you'll find your dream baby.