basically both jobs pay less than i'd think fair. and they know it. so they don't demand 40 hour weeks, there's a lot of telecommuting give, and i'm bloody efficient and have 20 years of experience. could i go find another primary position? yeah, but in other respects its an excellent job and will get better over time.
do i work 80 hours a week? nah? 60? probably. will i do this for long? no. i've got a desire to have a huge amount of cash in the bank, a couple with two kids in pricey preschool (it's not that pricey, nothing's cheap around here) and wife whose job doesn't pay well at all (she's part time and they pay her 12 hours for 24 hours a week of work... lovely... i love engineering). when one kid is in public school and i have my pile of cash, this madness will be done too. give it two years. since i've been doing it for three, it's no great big deal. is this good money? well, yes it is, not by steve's standards, but certainly by most americans.
crazy? i guess. then again, i come from an immigrant background and you know what, a lot of the people in my father's generation did the same. janitor by day, saved up and ran his own building in his spare time. accountant by day, cleaned carpets at night, worked in factory during the day, drove cab at night. plumber for big firm during day, plumber for little guys at night. moonlighting. well, i got no need to bitch about it. in contrast to what those guys did its cushy. just want some security is all.
re: os x server. i understand what you want to do, but i don't see how the hell you could do that without separate IPs for each site. now what you might be able to do is purchase a static IP package with say 5 IPs and then route them to your server and have it determine what you want. but it'd probably be a lot cheaper and better to just get a dreamhost account. or this might be cheaper, but your mileage may vary....
http://www.absolutely-free-hosting.com/reviews/110mb.php