I'm a new goat owner too and have had good success milking my nubian once a day and letting the kids nurse during the day. It really hasn't been much of a time commitment, milking takes 10 to 15 minutes every morning on top of my other morning chores and I lock her up in the evening when I have the time, not at the same precise time every day. I do get more milk when she goes to bed earlier, but we get 4+ pounds a day from that one milking so I'm not too worried. Last night they were separated for 13 hours and we got just under 5 pounds, or 2.5 quarts. I already have layers and broilers who need a bit of care every day so it wasn't a big deal to add milking.
I am paying my mom to come to my place and milk for me while we are on vacation next week, but other neighbors have offered to do it just for the milk if i take her to their place (they have goats too).
As for the money? As little or as much as your want to spend. The animals themselves are surprisingly cheap compared to the cost of setting up facilities, vet bills accessories and feed. I'm trying hard to cut down on my costs while still raising very healthy animals so we head to the scrap pile first to build new mangers and pens, scavenge fencing off craigslist, treat holistically using the methods in Pat Coleby's "Natural Goat Care" book (well worth the cost of buying) , and buy our dairy ration at the local feed mill in quantity for 11.50 per 50#, before the ton discount.
My vote is for the milker, I love mine.