@Adam Azam if the tenant is as far behind as indicated and their source of "potential" funding is as uncertain as a very speculative workers comp claim, they are probably going to owe the entire world money when/if they recovery anything in the future.

I hope all is well with you during these unusual times today.

I'm uncertain if this is a viable option.

I ask because it's unusual that the landlord would pay utilities.

It is also very unusual as a realtor, you working with a wholesaler and not directly with the owner.I agree with  @Wayne Brooks

To be fair, this is an unusual deal.

As investors, it's not unusual for us but most people don’t generally move from a nice single family into a smaller multi-family so underwriters will flag this. 

Should I A: stay with the 1 building paid off in these uncertain times with the ability to cash out laterB: cash out and buy local C: cash out and move to investing out of state building another team and maximizing leverage to increase cash flow and move closer to my goal of retiring from my W-2 in the next few years?

Im uncertain of the capital gain calculation and which form to report.

I've noticed that many new investors can find themselves uncertain when a potential deal presents itself.