I am 66 yo, semi- retired and able to work on line. I bought my first sailboat in June although I have been sailing all my life. I have taken many courses , done a flotilla with the wonderful OffShore Sailing School
( sailed with Fatty Goodlander ) and then with somewhat less than you have stated as a kitty proceeded over a three year period to research
, inspect and finally buy a boat. The boat is actually larger than I planned but the price
was less than the smaller boats I was looking at (45 DS). I found a boat that had been lightly chartered and got great marks from a very competent surveyor
. I have replaced the standard rigging
, stopcocks thru hulls, ad electronic and the boat is almost ready to sail. I am waiting for a new jib
as recommended. I will be a live aboard in a marina initially while I learn the boat. Be methodical :Every journey proceeds logically, one step at a time with the initial idea and inspiration. Make sure you love to sail and can deal with tight quarters. Then educate yourself in a way that is comfortable. Read information from the Forum and West Marine
on line and look at the youtube sailing blogs to see what others are experiencing. It is definitely doable.
Good luck, fair winds, following seas!