Can a landlord (or their lawyer on their behalf), ask for medical records in response to a reasonable accommodation?

I do not think asking for them is illegal. You have the choice not to provide them. As counsel stated: you must prove your damages.

Is this lawful to keep the tenant deposit if tenant want to terminate the lease 6 months in advance ?

Is the two parties agree to this arrangement then yes. This would be a valid agreement.

If you have proof of a unspoken contract through a text message in court will it hold up 19 years later?

Your question is a bit confusing with your description. Discuss offline with an attorney.

As counsel stated, you can file without an attorney or pay an attorney a minimal amount to file.

How would I go about breaking a lease due to my landlords inactivity in installing fire alarms/fixing a leaky roof?

I agree with counsel- notify the county. You could file a rent escrow and/or negotiate an early termination.

Technically the law states that the landlord must deposit the security deposit must be in a separate interest bearing account. Therefore the...

Have an attorney look at the file. It may be an error however you do not want a warrant hanging out there.

Yeah I agree with counsel, you can provide notice to vacate then file tenant holdover.

I have a tenant who is at the end of theyre lease which ends on 31 of this month ,i want to evict her and not renew lease

Failure to pay rent is typically the quickest way to get into court and evict. If you gave the proper notice to evict, you can file a tenant...

Can husband stay in apartment if wife dies and he wasn't on lease.

Yes you could try to attempt to negotiate a new lease. If not, then the landlord would have to file a petition to evict.