I'm considering assuming this mortgage, either "subject to" or by transferring the property into a trust, where I would then buy a majority share and cover the remaining balance in cash.The complication arises from the fact that this existing mortgage is a VA loan.

Transitioning to a new GC can also complicate the process as whomever takes over will likley not provide any warranties if applicable and you should expect to be charged a signficiant mark up.

My journey was fraught with failed contracts totaling over $180 million, each one a heartbreaking setback due to negotiations gone awry, inspection issues, financing troubles, or unforeseen complications.

It seems like this scenario is somewhat complicated but the property is also not high enough value to warrant a full-up normal cost seg.

I'm a firm believer that even the most complicated financial strategies should be able to be explained simply. 

@Kyle KlineDon't over complicate it less is more 

It's a bit more complicated than just using the capital gains. 

Residential contract aren't that complicated and do a few deals you can already know all the clauses in it. 

Things get even more complicated when you have multiple rentals and you end up having to use class tracking to try to keep them separate. 

This can get complicated if you are racing against time between getting it sold versus the banks take over.Can you get it sold at a high enough price to pay off the mortgage or is the owner under water?