What is the best way to extend my stay in Thailand as a Canadian expat with a non O (volunteer) visa and work permit?

Hello. I currently have a non o (volunteer) Visa and work permit. The Visa expires end of May and the work permit mid July. In June I am planning to return home to Canada for a short visit. When my Visa expires at the end of May, I will be leaving my volunteer position and giving up my work permit (cancelling it correctly). I am hoping to stay in Thailand until mid June. Is the best way to do this a quick land border run near the end of May and arrive back with a Visa exempt stamp for 30 days (Canadian)? After leaving Thailand, in Canada I plan on applying for a single entry 60 day tourist Visa to return with in July.

My question is, is there any risk doing a land border crossing or coming back with a tourist Visa after being in Thailand for a long time on a non o and work permit? I have been on 2 non o visas with work permit since 2015, with only one Visa exempt stamp from 2015 and no previous tourist visas.

Thank you for your advice!