To make a decision on the route to take, you have to do some homework first which entails, learning how much $$ you have/need for each, how much financing if any will you be qualified for, what's your level of expertise in either, will you have partners going in, do you have the team of qualified professionals for each.

You definitely should add an attorney to your team and speak with him/her about that in more detail from a legal aspect.From a tax standpoint, an LLC doesn't really do anything for you - your share of income/losses is passed through to you and reported on your individual tax return.If you have any other tax questions, happy to help.

would love to team up with an agent and build a great relationship for future investments 

@Leon Kanon Chicago is a great market for investing but an out of state investor like yourself needs to assemble a team first.

I am a Veteran first time home buyer, and I believe a quad would be a great foundation for this journey.I am looking for a realtor/investor preferably someone who works with a team, and has connections with contractors.

@Johnson Michael its all about the team.

I would love to look for my team perhaps through these forums, and I'd love to fly out and check out the neighborhoods.

But you’re the coach, this is a team sport.

I would have jumped on them if I had a team together but I've only been in the area for a year.I'd like to get in to a duplex house hack but those on the market won't cash flow. 

Being new you want to use the credibility of your power team.