But I would remain open to long-term rental as an option as this seems like a more stable option in terms of income, again this may be my inexperience talking.However, I have always  been somewhat risk averse and investing in real estate is always a big venture, in my opinion/experience, in terms of capital.

Here’s our OPINION for the Metro Detroit market (use as a template for your target area!)

The real pool season is 3-4 months, which also sways my opinion. 

Taking the risk of a tenant while you yourself are renting is not optimal in my opinion.

In my opinion though, I would not touch your rental. 

@Huong LuuIn my opinion, presuming you need the money - it is better to cash-out refi the property.  

In your opinion, would someone be considered an expert after completing 2-3 'smaller' multifamily deals, or is it more like 5-10 deals?

That is cheap to install 2 units in my opinion. 

In my personal opinion, I think the return of 100% bonus (or at least expanding 179 a bit) is somewhat likely with the new administration, so it might be worth it to you to hold off on doing anything until things look a little bit more concrete.

Charleston (in my biased opinion) is one the best places to live in the country.