@Matt PippinIt sounds like you're at a pivotal point in your financial journey, and considering real estate as a means to further your goals is a smart move.

Use your savings from not paying rent to buy another property within the next few years and your on a role.  

I think you might be at a point where comfort for you and your family should play a bigger role than it did before when it was just the two of you. 

I've been here for a while reading up and am excited to make my first post.A bit about me, I am 30 currently making a great salary in a W2 contract role that I will likely remain at through this year, after which I expect to look for a more permanent role with a lower base salary, however likely similar overall once benefits are accounted for.

Currently, my role is managing all the systems and processes for our company and when the website was made it was all tech-related systems, now it's the entire org so I need to update it.

In addition to my role in mortgage underwriting, I also own a duplex, which has significantly fueled my interest in the real estate sector.

For further context, I am not taking on the role of a silent partner in the company.

On the contrary, if an exec board has 50-100 years+ of experience they likely have seen some adverse economic cycles and know how to pivot in such environments. 

I was able to BRRRR four properties there and now i am slowly deciding to pivot to tackle more appreciation plays.If your first rental is an appreciation play and there simply is not enough rental income to offset your expenses then you may run into financing issues after your first property.

It sounds cheesy, but the best way to prepare is to work with a friend or two and role-play.