My co-worker does this and his brokerage is known for training new agents so I was going to check out their programs.Pros: Gain experience in real estate buying/selling, earn money, network, obtain real estate licenseCons: I have to pay for training, etc.. so I risk losing money if I cant do any dealsI would love to hear what you guys think about these two options, do they sound like something I could realistically do?.

Inventory is tough all over the US right now.. 

That sounds like a tough model to work with.  

With the way the market is now, one's time, and even money to invest, are a commodity .... it will be tough to find a mentor/teacher in this way. 

Hey Chris, that can be tough as being paid should be your top priority (which it sounds like it is).

You could be on the hook for some pretty big repair bills with contractors or you’ll need to add in a maintenance worker. personally, I wouldn’t touch it at this price, on what I know

If you're in a tough spot, do what you have to do, but then find a way to make more than you spend so you can pay down that HELOC.

Do your property management companies require you to buy workers compensation insurance?

@Jeremy Salo Its tough for someone else to tell you what the "best" strategy. 

Extremely tough to get listings.