This forum is for simple and general questions, not a substitute for legal and accounting advice. You have surveyed professionals of different disciplines and gotten different answers. You have also done your own independent research. It is time for you to decide what is right. To be safe, why not file separately during the conditional discharge period?
Posting questions anonymously and receiving general answers do not substitute for consulting with an attorney licensed to practice in the jurisdiction in which you live. Answers posted here by Kevin C Gleason are only intended for general education of the public on legal matters. Please consult a qualified professional before deciding what to do about your situation.
Your questions are way too complicated to be answered in this general forum. You need to sit down and meet with a CPA or tax attorney so they can review your entire situation.
The above information does not establish an attorney-client relationship and is based upon the limited information the questioner provided. Unless you have signed a representation letter and paid a retainer, you are not a client of the firm. You should seek legal advice from an attorney in your area if you want a full legal opinion in this matter.