What do you believe to be the biggest obstacles house hacking investors must overcome?

My biggest piece of advice would to always disclose that you are a licensed agent when discussing with potential buyers of properties you own, and potential sellers of properties you would like to buy.

One of the biggest wake up calls I had was with my first property and first tenant, walking into the house after she moved in to look at a couple small repairs that I missed in my rehab when I bought. 

Without relying on local realtor CMAs, which they have little incentive to really provide good data for, I am looking to pay a reasonable amount for an appraiser to povide a more confident ARV in the various markets we are searching. 

If extending it is the right play for you (risk wise) then I would find a way to sweeten the deal for the sellers, otherwise where is their incentive to play nice and let god knows what happen to the property in the next several months knowing its vacant.

That to me seems like the biggest win you could have right now.It's a big risk right now proceeding, I think, based on what you described.

How many renters stop paying is the biggest wildcard for me and my investors at the moment.

Rent is probably the biggest expense of any household.

The biggest keys in Real Estate Investing is to Buy It Right and Sell It Right.

I think the biggest thing to address first is that you likely would not be able to use a VA loan on this deal.