Becoming a real estate agent is a good idea to gain experience, but you could also explore property management, wholesaling, or working with an investor to build your network. 

If anything, at least wait a year so you don't pay short-term capital gains on the sale of the property.I need to find some more deals like that here in Chicago...where in Houston was this property?

I gained equity in the property, and I got higher rents which lowered my living expenses while living there.

I would think with the HELOC, I could run with that until I can do a refi and with the interest rates starting to come down, there should be some gains to be made and I can repay the HELOC in short term. 

Really just trying to build a solid base and gain as much knowledge as possible and eventually specialize in something.  

Real estate is basically an income producing and or capital gain producing investment.  

I also don't want to show any type of distrust towards her as I feel that she is a valuable asset (if she is what she says she is). 

No capital gains in Belize.  

Would the LLC need to prepare a partnership return for the dividend income and capital gains?

In areas with rapid and sustained appreciation, you can use the equity gained through appreciation to purchase additional properties.