Sooner or Later (a boat)???
<ol>Buy the small boat now:
<li>You''ll get to sail now.
<li>If you buy well, the money is safe until you sell.
<li>Even with dockage & maintenance, your "big boat" kitty will continue to grow while you''re out on the lake.
<li>You will likely adjust your "big boat" timetable as you continue to exhaust the possibilities in the small boat, and wind up having more money for more boat when it''s time to move up.
<li>You will improve you sailing skills much faster on the smaller, more responsive-but-more-forgiving boat, and so be more "ready" for the bigger boat.
<ol>I see nothing but win here. Just don''t:
<li>Pay your friend more than local market value, including factoring in sail condition, or you''ll take a bath at sell time and it will cause bitterness and resentment with your friend (how could it not?).
<li>Lose your vision for the big boat and start pouring money into upgrades, bells and whistles that will be "money lost" when it''s time to sell. Save that $ for the big boat.
If you and your friend can''t agree on a fair price that relates to "blue book," the idea of buying a popular small keelboat now might still make sense, as long as it''s something you can easily sell down the road. At the risk of sounding insulting, it''s not your job to make his life easer. Pass on it if it''s not right for you. The friendship will survive.
Or you could just continue to crew on your friend''s boat, and save $ at a slightly faster rate.