I would strongly recommend going the option of @William Collins and here is why: It is the easiest and quickest path to getting money in your pocket.

just looking for advice on what path to go down

I would reach out to @Steven Hamilton II or  @Jake HottenrottThey both are real estate specalized and work with clients across the country.

I'd love to connect with some BP members that have already walked the path of long-distance real estate investing and talk through how they chose their market and how they set up systems that lead to their success. 

The first step I would recommend is to get on the same page And set the goal. from there the path probably isn't incredibly different depending on equity on the house you bought you might try and refinance and pull money out for a down payment on the next property whatever property that is.alternate methods of buying another property would be things like seller financing hard money private money or if you have the means obviously cash.But seriously the best thing I can tell you is to make sure you guys are on the same page and pushing towards the same goal If you're not it's going to be miserable

Here in the Chicago area, we do have higher property taxes than in some areas of the country.

If neither, do you see a path of development that will eventually bring utilities at least close by?

Anyway as mentioned above, I am looking to volunteer my spare time in hopes of learning a thing or two about the real estate space to see if it is a path that I really want to invest time and money on (without blindly purchasing a property and learning the hard way).

Fist off, most "credible" listings on the MLS all over the country right now, either go extremely fast or can, and are usually overpriced, compared to a year or two ago.

I am currently working out of the country and have struggled to find an agent willing to work with me from a distance.