Let's put this into some context: Let's say there is 12 million illegal immigrant's in US today. 

Welcome Nish.You are making a good decision to get into real estate.

I’ve been looking into areas like Oakhurst, Mariposa, Yosemite West, and surrounding towns.If you own or manage a vacation rental in this region, I’d love to hear about your experience.

I'm interested in flipping, and short-term rentals at the moment to build good cash flow, then pivot into more of a buy-and-hold/appreciation play 10-15 years from now.

RESOLVE this issue NOW and make a clean break. 

One is under contract in which I plan to 1031 into something larger and the other I just plan to keep as the contract expires soon.

or move back into the property?  

Yes, I definitely see a lot of situations that break even or go negative.

B class will be basically break even maybe slightly positive cash flow on a good deal with your typical 20% down payment and financing the rest with todays interest rates. 

Look to other members suggestions and, definitely interview your Realtor choices before going headlong into an agreement.