I've noticed different options do vary with different states, for other venues. have no experience with SSDI, however i know what you mean by assets- SSDI would be a better choice than other SSI
however hearing loss is very hard on anyone, was wondering if you learned sign as you mentioned you were HOH before. That could benefit you with sign language interpreters as its much easier than lip reading in my opinion however if you can hear well with hearing aids it would even help you succeed.
Another factor that could be hurting you in job seeking process is that youre an older person- its a hidden discrimination not alot would admit it, many want younger people in some areas for different reasons as cheaper wages and more knowledgeable about technology and so on....
However, kudos with you wanting to go back to school, shows the rest of us its never too old to go back! It really depends on what state and what assistances you can get for going back to school also as each state has their own rules.