Am I in a bad position.

However, appreciation will put more dollars in your pocket over the long run.The best solution is to find a property with positive cash flow in an appreciating market.

Does anyone have experience of setting up a STR while in the same position? 

Ideally looking to cash flow positive on all properties.  

I'm looking to finance the project long term in a way that is helps me create positive cashflow.

Given that I'm not positioned to buy just yet, and simply running the numbers, is there a rule of thumb for estimating insurance costs that would make sense in Cook County?

Main goal of All In One heloc or 1st Lien Position Heloc:  Lower your daily average balance.Main Drawback: Rates are substantially higher than 60% of current 1st mortgage balances.If you are mostly living paycheck to paycheck and your money leaves your account as soon as it comes in to pay bills, this is not for you. 

I’d also love to hear your predictions for how the real estate financing landscape might shift this year and how you plan to position yourself for success.

He'll have at least $2k per month in positive cash flow and tons of equity when it's time to find the next home in some years.

I don't know where to invest, really drawn to Columbus for many reasons (some cash flow and stable appreciation)--what's been some people's positive and negative experiences in Columbus?