Idk if I should shoot my shot

Ok so there's this guy that I like (I am also a guy) and we've known each other for 5ish years. I came out to him as transgender (ftm) about a month ago and hes super good with it, and told me that' hes bisexual. We went to elementary school together, and got split up in middle school but still hang out all the time. I've had on and off feelings for him since we met, but lately I've been crushing on him again. We have a lot of history and he's one of my best friends, plus has shown a lot of signs that he likes me. Here's where the problem comes in.He goes to a different school, and we can't text because his mom is really protective and doesn't let him text or call anyone he isn't related to. She fucking sucks.He lives about a 15 minute bike ride  from me so we could still see each other basically whenever we want, but idk if it's worth it to get in a relationship where we can't text, call, and don't even go to the same school. But I like him so much he's genuinely adorable and really sweet and funny. I've liked him for 5 years at this point. Do I shoot my shot?