Neither the presence of ketone nor the double bond is problematic when conversion of an acid group to ester is sought. The trouble is that your compound has a hydroxy group which will compete with any alcohol (R-OH) while esterification is carried out, i.e. the product will be 2 different esters (the one you desire & the other one formed by every 2 molecules of your compound one using -OH while the other using -COOH) since esterification is basically an interaction between the 2 groups whatever the source of -OH is.