toe overlap is something you get used to and work around. the brake, switch out the fork if you can.

if you think you need a brake, you probably do. that isn't necessarily true, but i'd err on the side of caution.

just so you know, i feel like a hypocrite saying that. i started riding brakeless when i acquired a track bike and had no way to get it home but to ride it or walk it or take public transit (**** those last two), plus my companion wanted to go get pizza. i wasn't confident in my ability to ride brakeless, but there wasn't a lot of traffic, and i was a little scared, so i was looking for it extra hard. i got used to it enough after maybe 3 or 4 days, and it's all been intuitive from there on out.

that said, i can't tell you it'll be that easy for you. so err on the side of caution, if you're not sure about riding brakeless.