or he'd pay to work?
i did not read all the comments but i had done cage wrestling with servers as a week long event as well as those mid-night cravings that i need to touch the servers just because they are not purring at the right frequency. in addition to all the power, connections, server survival conditions, server security, assisted monitoring (don't rely solely on anyone), etc etc. i also find the need for good nearby parking, large clean bathrooms, available stools or chair, tool set(sockets, big screw drivers, pilers), a place for a coffee break, scream at the VAR and making excuses to the spouse, ULTRA HELPFUL. for small setups and fuzzy architects, these are something as a tech look for in my experience.
486 in the days of i7 is it really worth your time? even if you revive it, the second you hit its limit the second you wish you had not spend days trying. the issue is that all other software had moved on. i tried it with a 1 gHz P3 toshiba laptop, but then it couldn't even play youtube videos in decent smoothness. DSL/kubuntu what not, it's just not worth the two days trying various distros and drivers, compile my own drivers to make it work at a frustrating fashion. go shop craigslist.
if you are truly going with the "start-up" mentality then expect things in bad shape at the beginning. i would suggest you raise the funds to do IT right if you have an idea (IP) that is worthy of such. if not then talk to your friend to find some trustworthy IT folks. i hope you are not developing on an island. don't hire because "i need it now". the costs of subsequent fixes will blow your mind if not your start-up altogether. think about a comprehensive NDA and make it bite.
use the other "start-up" excuse and use bleeding edge technologies to keep your IP safe. TrueCrypt anyone?
if you just worry about being hired later, review your own hiring practice. what do you look for when hiring? does age matter in hiring a developer? how about management position? there lies your answer.