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. 

Ideally looking to cash flow positive on all properties.  

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

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.

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?

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? 

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.

Some will be ok in 2nd position and some will not and force you to refinance out the first - but those are options that are probably cheaper than credit cards 

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

If it's net positive, then make sure to do it up to code, etc so the finished square space can count.