This is a how long is a piece of string question... There are many ways to eat an elephant.
1 - Decide how much money you have and live within those means for the sailing experience you can afford.
2 - Decide the sailing experience you want and create a budget to fulfill
You have a budget. I personally think 36 feet is more boat than you can afford. You talk about being in a marina (where you are) for 3 years so I am guessing coastal cruising and weekending.
I would go with a 27 foot plastic boat - Catalina
- Handling easier
- Costs easier
- Berthing cheaper
- Hauling cheaper and more locations
Invest in getting it the way you like it. I have a 1982 model 25 1/2 feet (I always count the half - Ha) - I wish I had 27-30 foot max (for now) - after 30 feet I lose a couple of haulout locations around here. 25 (and a half) feet has provided hundreds of hours of joy.
My costs are no real reference for you but over 4 years we have spent about US$500 a month for everything all in. Insurance
, berthing, maintenance
and upgrades. We spent about 1/3 the purchase price
in the first 3 months getting things up to spec.