I remember them saying something about not being able to do a simultaneous.

With houses appreciation continuously over the last 30 years, and the increased construction while simultaneously running out of land to build on, does it make sense to hold onto the property every year (while losing potentially 5k/year to break even and for rental income GET tax) and bank on appreciation?

Attack both simultaneously and independently.If it were me, I'd get more than one GC out there. 

This would have been for 2 simultaneous rehabs of two homes.

Sort of simultaneously ?

Is it able to support the demand for both units simultaneously?

I entered the job world as an office manager for a local real estate office, while I simultaneously started my own wedding invitation business.

That allows me to leverage the money more by getting a bigger property and simultaneously taking a big chunk out of the monthly mortgage payment.

"Simultaneous" close of two stand-alone transactions and back-to-back close of two stand-alone transactions are all that is permissible these days, generally speaking.

Another option is to look for a local note investor that is willing to buy the note at closing ( aka a near simultaneous closing).