It's very possible your Jeep Cherokee in fact needs more repairs to pass the smog test. It appears this smog technician is conducting repairs and baseline testing one repair at a time. If they are not continuously charging you diagnosis time, this is ok.
It is not uncommon for a smog technician to conduct several "baseline" smog tests after performing repairs. We would only recommend you work out a diagnosis estimate with the smog station. The smog station should either charge a flat fee for diagnosis (usually 2 hours of labor rate) or advise you that your Jeeps smog check failure diagnosis will be difficult for certain reason(s) and they can not guarantee the total job will cost less than "x" amount.
Other than that, if you feel comfortable with this particular smog repair station, and they appear to be honest and informed, continue you on with their recommendations.