Given your situation and concerns, here's a breakdown of considerations and advice:Pros of Renting Out Current Home and Buying a New Primary Home:Living Condition Upgrade: Moving to a larger, newer home with boutique features can improve your living space.Rental Market: West Town in Chicago generally has a strong rental market, which could provide good rental income from your current home.Portfolio Diversification: Adding another property to your real estate portfolio can enhance diversification and potentially increase long-term wealth through property appreciation and rental income.Cons and Concerns:Interest Rate: The current interest rate of 7% on a new mortgage is high, and there's uncertainty about future rate decreases.

You should only have to change when your current software has a flaw or lacking feature that is causing you to spend too much work on a work-around.

Realize that would be based on your efforts, versus the current sellers, but you would be willing to pay above market if you plan to make a lot more by doing the value add.I prefer to pay below market, but if the zoning is hard to find, if the potential value add is great, or the finance deal is wonderful, then I would pay above market. 

or it is just the way the market currently is right now ?

Currently rehabbing but need to refinance soon.

The current owner has offered to put up the down payment and add that onto the total price of the house so they’ll be paid back and we aren’t putting anything down.

I am currently a healthcare provider and hoping to use RE and other investments to create more passive income and perhaps retire early to spend more time with family and travel.

So I figured that I would create a post and say what I know of the VA benefits from what I have used for getting my current home and then having others add in to it. 

@Jeff G.If you only look at one meteric, look at Median household income.

I actually am only looking at resales that are currently managed by MSHB b/c I have not found another PM company that comes close to meeting MSHB.I've had one tenant for 12 years, I feel like at MSHB they different areas (maintenance, current leasing, tenant retentation, etc) really talk.I'm currently dealing with a nightmare with another PM company.