If I were in your shoes, I’d keep underwriting deals until you find the one that pencils best and lock it in while you’ve got the VA eligibility

You are not alone in the way you approached this home renovation, many in your shoes struggle with the same issues on their earliest renovations but the real lesson to be learned is to vet your contractor and take the time to execute a contract that covers timelines, payment schedule, scope of work, finish spec allowances, insurance, warranties and a number of other key contract provisions intended to protect you.

Hi Justin, I'm a local Chicago real estate investor who was in your shoes just a couple years ago. 

So if you were in my shoes and wanted to quit the 9-5 in five to ten years to pursue other passion projects, how would you go about it?

Wow, I’d be just as frustrated in your shoes.

I’ve seen many investors in your shoes wrestle with the same tradeoff: short-term cash vs. long-term stability.

If I were in your shoes, I’d focus on two things right now: building hands-on experience with a smaller property like that duplex and surrounding yourself with people already playing at the level you want to reach.

There were a lot of people who were doing a cash-out refi because it was easy money, until the other shoe dropped. 

It gives you focus and makes it much easier to recognize the right deal when it comes along instead of second-guessing everything.I’ve been working with newer investors in similar shoes and I’ve found that having someone in your corner for accountability and guidance really speeds things up.

If I was in your shoes I would worry more about the debt side, paying off credit card  or whatever debt you have in that 20k which I'm guessing if from the car note.