However, my debt to income ratio with that home loan, and student loan doesn't look that great currently and I don’t have much for a down payment.

I am currently living out of state so I have hired a property management company to handle this task, however, my home is still sitting vacant with very few prospective tenants.

Currently renting both apartments for a average monthly cash flow of $1000 Lessons learned?

Nice to meet you (electronically).Currently renting a single-family home in a very expensive coastal Southern California city.

I'm currently working in commercial real estate sales, but would like to work on my own portfolio with my wife.

Question: your current model worked well.

If you have multiple LLCs, best practice would be having a Plus subscription.  

We currently still have the AK condo rented out and have bought a house in Phoenix that we are currently are fixing up. 

Set clear goals, save for a down payment, and practice analyzing deals to build your confidence.

Here in Chicago, you should expect a range from $200-$275/SF, depending on the location, experience, labor, and material finish level.Are you in a position where you already own some land, or what is your current situation?