Not long, and not much compared to most "contemplation boats".
$1k for the new main
$200 for a used Avon Redcrest inflatable dinghy
$170 for the boom cover I'll be buying today.
$50 for a set of brand-new genoa cars that my neighbor can't use.
$150 for the USBoat unlimited towing service.
Some hundreds for:
New fuse block and sundry electrical items, switches, etc.
New bilge pump(s) and associated discharge hose
New VHF antenna
New running rigging and mooring lines, various shackles
Harnesses and tethers
Most of it was just sweat equity. I'm am vividly aware that my situation isn't typical and that I was extremely lucky considering that I didn't know some of the key problem areas to inspect until AFTER I bought the boat. (Duh)
Also, the previous owner left me with a nearly new outboard and piles of spares, tools and hardware which has definitely reduced my expenses. I also own a full complement of tools, my boat is kept 5 minutes' walking distance from my house and berthing for it is dirt-cheap. Only a perfect convergence of circumstances has enabled me to enter the world of sailing so relatively painlessly.
Fuse block and re-wire: One weekend
Bilge pump and discharge: One weekend
Srubbing/cleaning: Two afternoons
VHF antenna: One morning
Rigging inspection/Running rigging replacement: About 3 days
An indeterminate amount of time driving around for parts.
I still have plenty of work to do and money to spend though!