The insurance companies will dig deep and will not accept you if you do not give names, addresses and phone numbers of all Doctors, Illnesses and Medications. There is no getting around their questions.
It took me over an hour to just go through and answer their questions for each individual illness. If you do not answer as far as who has been seen for the illness, and type of medication prescribed, they will deny you.
Even being seen for blood pressure brings a whole new set of questions. The information is kept on file. It does not matter how long it has been since you were seen by a doctor for the problem, you will be denied.
The company I applied for to continue coverage I had been with preveiously, still turned me down after caring for me for almost 20 years.
The company applying to will also ask for past insurance information and will get the information from them as far as care, Doctors, etc.
They generally do not ask what pharmcy you get your meds from, but each company may slightly differ.
In the most ideal situation the Pre Existing Insurance is the best chance of getting insurance with what you have explained.