1994 is not Clinton's fault -- the trends were well-established for a decade prior. The Democrats in congress were corrupt, scandal after scandal compounded by a very strangely cobbled-together coalition. Furthermore, the failure of UHC by Hillary was not due to any particular failing on her part, but an extraordinarily well-funded, savvy media campaign by the insurance companies, the drug companies and the medical industry as a whole, aimed at stopping UHC at any cost. Only now that the normal health system has gotten so much worse has public support solidly swung enough to make UHC practical to try again.
I used to live in Silver Spring -- now I live about an hour south of there. I think Maryland is kind of like New Jersey -- it usually polls better for the Republicans than it ends up. Just look at what the polls were saying for O'Malley and Cardin this last cycle for example -- both of them ended up hammering their Republican opponents despite 'neck-n-neck' polling. Thanks for all the effort!
Section 1 is as you summarized; if the resignation happens before January, there will be a special election within 90 days. If not, then the election will happen on general election day.
Section 2 says that the governor may (which in reality means will) appoint a replacement for Lott. This replacement will stay in office pending the results of the special election (which may be on general election day, provided that Lott retires later than December of this year).
I dunno, in a race where Kleeb seems to have next to no chance, I'd rather waste a nut's money running against another nut than use our money in a hopeless battle... Can't Kleeb run again in his own district, where he has a prayer of victory?