$2700 is precisely what you need to get started in pinball, and not a dollar less.
Purchase in this order:
Recommended Starter Kit ($900)
$450 penguin cart from penguinamusement.com
$300 tools (see pinrestore.com and get almost everything up there under "tools")
$50 cleaners (novus 1-2-3/wax/metal polish/brushes/rags)
$100 beer for when friends come over more often
$1400-$1600 for a nice Diner / Taxi / Grand Lizard -- any fun system 11 from 1986-1991 (There are about 25 great machines to choose from in that era). Perhaps for your first one, try not to get something with deep layered ramps that will take you forever to disassemble to change a bulb or rubber. Go for flat and simple playfield on the first one to get your feet wet.
Small Parts that match your machine ($50-$300)
$50 for bulbs/rubbers
$25-225 for replacement ramps, minor broken plastics, etc.
I just got started 3 months ago, and if I didn't have what's in my Starter Kit (thanks to my friends pushing me to invest up front) -- I'd be a very unhappy man. I've purchased four machines from fair to very good quality and have implemented 10-40 fixes in each one. Have chosen to repair ramps than buy new ones for $100. But I keep the cash on hand in the budget for each one in case I go that route.
You say you don't know how to repair machines. You'll want to distinguish "repairing" between diagnosing backbox motherboard/power/wiring diagnosis/repairs, and playfield repairs (aligning/rewiring switches, and cleaning/waxing/replacing plastics). Most of the playfield stuff is well explained on the internet -- how to repair/replace/polish/clean/wax, etc. I encourage you to treat this like maintaining the interior/exterior of your car (easy and doable). Treat the backbox repairs like working on the engine block (let a repairman do that). So definitely arm yourself with tools for all the playfield work -- it's very rewarding and for the most part -- easy.
And finally, I'd say tuck away another $1500 for your second pin. You'll want one you can play while you work on the other. Oh, and once you've done that, sock away another $1500 for the third one, and then after that...