F-1 visa Expires

So I Am waiting on my STEM-OPT Extension and my F1-VISA Expires in Oct 2020. Now I’ve heard through many that as far as I have my I-20 updated with STEM-OPT period until 2022 I should be fine working and continuing on that even if F1-VISA expires and try on getting through with H1 application through employer but what if my F1 Visa expires, and H1 isn’t applied or if applied not approved. After F1 Visa expiry, can I re-apply for another F1 for another degree I plan to do after STEM-OPT?