I am not the expert or have knowledge in mediations, but I am pretty sure
that in term of mediations, they do not look at the history. They are only
concerned about current medical status. I'm sure that you know that some
medications are forbidden in aviation. I do not know if any of medications
you are currently taking are forbidden. Here is what I found on FAA
website:

6. What medical conditions does the FAA consider disqualifying?
The following conditions are listed in the regulations as disqualifying
medical conditions; however, in many cases when the condition is adequately
controlled, the FAA will issue medical certification contingent on periodic
reports.

1.. Diabetes mellitus requiring hypoglycemic medications
2.. Angina pectoris
3.. Coronary heart disease that has been treated or, if untreated, that
has been symptomatic or clinically significant
4.. Myocardial infarction
5.. Cardiac valve replacement
6.. Permanent cardiac pacemaker
7.. Heart replacement
8.. Psychosis
9.. Bipolar disease
10.. Personality disorder that is severe enough to have repeatedly
manifested itself by overt acts
11.. Substance dependence
12.. Substance abuse
13.. Epilepsy
14.. Disturbance of consciousness without satisfactory explanation of
cause
15.. Transient loss of control of nervous system function(s) without
satisfactory explanation of cause.
Now in term of DUI, under parts 61 and 67, FAA may deny an application if an
individual has had two or more alcohol-related motor vehicle convictions or
state motor vehicle administrative action within a 3-year period. You had
DUI in 2000, which is more than 3 years ago. I believed that you are cleared
in that case, but you still have to report it.

I hope this information will guide you to the right direction, but keep in
mind that I am not the expert.

If you are not familiar with sport pilot, you might want to look into it in
term of requirements before you apply for medical certificate.

Toks Desalu
PP-ASEL
Dyin' to Soar!