Since then I’ve saved enough up to get out of the renting cycle.

.- Condo Board President of 32 unit building- Sales and Service District Manager for automotive manufacturer- DIY - home improvement enthusiast

Anything less than $875k (less selling/closing costs) becomes “boot” and is taxable up to your total cap gains and depreciation recapture.To avoid tax, 2 rules.1) replacement property price must equal/exceed the sold property2) you must reinvest All the cash proceeds from the sale

On one hand you have a lucrative sale available to you. 

I recently came across a 5 unit property for sale, a tri-plex and duplex being sold together on the same lot. 1st question, in terms of conventional financing could I consider the buildings seperate and get a blanket mortgage for two residental buildings?

But the property gets reported on the joint return just like yours.Some clients will prefer to have a "quiet title" transfer done right before sale so the deed matches before sale and 1031. 

If seller goes under contract with another offer, do you believe judge could award the sale of the property to us?  

I am also considering learning wholesaling considering that will help me acquire capital faster than just having my M-F sales job while also learning more about real estate.

The house we rented out has $157,000 in equity based on current estimated sales value and our other house we live in currently (we just had appraised) has $130,000 in equity. 

A Lease Option is not a sale so you probably don't have double closing costs.