You would need to remove the existing siding to apply new siding. You do NOT put it over the old. That's a hack approach that leads to all kinds of issues.

For the cost dference, hire an actual professional painter to do the job correctly. Basd on the provided information, I'm betting on you using an incorrect primer. Probably something water based. I'm also betting that you didn't lead test, or do the proper abatement removal techniques.

thank you Sophie! After reading many articles as to why paint can fail I'm sure there is some condition specific to my house that is causing my paint to peal. I did however use an oil primer and then two coats of latex. I also had a lead test conducted, which was negative. At this point I'm done with paint and on to other options.

Latex paint will not adhere to oil-based, so that was probably your problem. Did the experts advise using oil and the latex? Maybe I'm wrong, but I painted interior doors and the paint did not adhere properly.

I suggest that it would be worthwhile to talk to one of the best professional painters in town. Ask an active real estate agent for references if necessary. There can be incompatibilities of oil based primer and modern water-based paint formulations, especially in areas where air pollution controls required reformulation of paint. If you are "done with paint", try finding a general contractor who can deal with removing the entire outsides, insulate with appropriate material, and then put up new siding, stucco, or whatever you choose.