Seems like a relatively low-risk and low-maintenance entry point into boating. I'd try watching some youtube videos on prepping your boat for the season and see if you can figure it out yourself. Expect it to take effort and patience (and a bit of money).
Don't forget about life vests...
I have a decent FAANG (+Microsoft) investment I've been mulling over. Sell high or see if it goes higher? Are these tech stocks 20 year investments or bound to get replaced eventually?
My advice to someone with toddlers is to wait a couple of years. When they're 4+, you can do your morning workout and not have to worry that someone might die if they get out of bed while you're busy.
T25 on BeachBody is a great full body program. Just don't expect to drop 40 lbs in one run-through (14 weeks) unless you strictly follow the diet plan.