School is a good time to get transition over and done with. I wish I had gone that route. But I don't know that I would've quit my job to go back to school and have time to transition. Having benefits and a stable income has been absolutely integral to the success of my transition thus far.
The services that I access for HRT cost me about $120 for my copayment, lab work copayment, hormones and needles. That is for 3 months worth of stuff. If I didn't have insurance I'd have to get on the sliding scale at my doctors office, which can take several weeks. If it wasn't planned at the proper time, I might have to take a few weeks off of hormones. I'd also be paying a small fee to the doctor, the same amount for hormones, and over $500 for bloodwork that then wouldn't be covered.
It presents a very different logistical picture without benefits. And if nobody administering HRT in your area does a sliding scale for low income patients, you will burn through money quick.