While you are
learning, have you considered getting a smaller
classic, like a Triton 28 or
Alberg 30? Those
boats can be obtained inexpensively in good condition for $8k to $15k perhaps including a
diesel or overhauled Vomatomic 4 and have sufficient
headroom and living quarters especially for a bachelor.
They have simple systems, no liners to conceal costly structural problems and are relatively hard to lose large sums of
money on for updating deferred
maintenance. By reading
restoration blogs you can familiarize yourself about their usual pitfalls. Also, they would be much easier to learn how to sail singlehandedly. Moreover, if you really like the simple/outboard/inexpensive
route, James Baldwin's blog details how to install a 6 HP
outboard in their stern lazarette.
Compared to a 30 foot
boat, everything about a 40 foot boat is much more complicated and expensive. It is important to understand that a 40 footer without an
engine may not be a good deal even if it is free especially if there are other deferred
maintenance items.
No one has explained why a large boat does so poorly with an outboard, except to point out they do OK in totally calm conditions with no
wind or
current. A 40 foot sailboat has a lot of "windage." Even with the
sails down, it will be pushed about by the wind. In 10 knots of wind, when the boat gets turned 90 degrees to the wind, the wind often has more of an effect than your
propulsion system- you turn the
wheel and nothing happens and the next thing you know you are in a very awkward situation. At the critical moment, the
novice panics and hits full throttle leading to an over-correction which causes the boat to hit whatever it is aimed at harder. Also, in any kind of wave action the boat will hobby horse somewhat causing the outboard's
propeller to cavitate or come completely out of the
water. The worse the conditions, the less
power and control is available.