Question about getting a second mortgage and short term rentals

[Brady Ingledue]

Hi BiggerPockets people!  I currently own a 2/2 condo that I have rented to a buddy for about a year while I have been renting *shudder* a house.  Both of our leases are up in about 6 months and my plan is to buy another condo to move into (for a year and then rent it out, rinse and repeat) and try short term rentals with the existing one.  Would I qualify for another owner-occupied mortgage?  Do I have to show that I could afford both mortgages even though I plan on doing short term rentals with one?  For context, I make over six figures and have great credit.  Any insight would be much appreciated...thank you!