All, I am new to the game, have one rental property thus far. 

Maybe getting your license will expose you to others who are also new, and looking to get into the game?

There are a lot more older homes that could use updating, which would allow you to use your construction skills and enter the real estate game.

As long as all involved know the rules of the game and play accordingly. :-) 

In my opinion, I think it's important to devise a game plan that works for you and your family's goals in real estate. 

After the game, we went to her rental apartment which, while her apartment is really nice, is in a building that is clean but has a very 1960s feel to it... it's really dated for the wealthy area it's in.Once we were inside her apartment, I told her, "Here's what you are going to do.

With a LO you get a tenant with skin in the game ($9k option consideration in my case)  and a commission-free sale with no vacancy. 

But that's a long game I'm not quite committed to yet. 

Real estate is a long term game, so timing a purchase for the Spring or Summer may be less advantageous than say buying in the Winter.

Often times, we find red flags during the detailed analysis that kill the deal (most of the times, it is major repairs needed) but that is a part of the game :)