You can hide your reputation in the residential world.  

Create a plan to go out to a new area every couple of days to explore and see the situation for yourself. 

@Joe M.The education from BP and most other reputable sources always taught to keep reserves.  

All in all I would explore every option I can to get that unit cash flowing.As for the Finance section of your deal, your worst case is you may not be able to refinance the property right away.

My name is Frank and I have gradually began exploring real estate over the last few weeks as my curiosity has grown of what to do with my financial stability and overall savings.

Right now, I'm in the exploration phase where I'm specifically looking to house hack a duplex or triplex in Middletown, Bear, Newark, Hockessin, North Star, Pike Creek, or Greenville.

This is something that I would recommend exploring and may be something the seller would understand given the circumstance.

Hiring out to a reputable company helps with underwriting.Finally, to answer your question: how likely? 

Find a way to make it happen and explore all options. 

I have always been very risk adverse with finances and something clicked in 2019 to start branching out and exploring other possibilities, so here I am.