We understand that vacancy is a true killer to an investor's portfolio, and we track multiple metrics to keep abreast of any potential concerns.

If there are any specific videos concerning using VA loan that would be helpful.

I encourage them to purchase travel insurance if concerned.

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.

The AC company said the dripping usually happens before leaking. 

It's difficult to really comment and address your concerns without more info. 

The policy they put into place might have a small percentage change, but nothing large enough to be concerned. 

If you have any specific concerns, I'm always down to chat on them or any other insurance topic!

Concerns?

I am specifically concerned about point @Richard Lee is making.