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.

I I spoke with a rep about the DSCR and he is saying mid 7s maybe a bit higher for loan interest rates. 

The redemption rate was 8% on the taxes plus some portion of the overbid.

Our interest rate at the time was still very reasonable and it was something I wanted to lock in from the jump.

Additionally we've found several local lending partners with credit unions that have supported and provided funding for unconventional and difficult property types to finance. - Costs and Returns : In overly general terms the cost of doing business in Oregon, (especially on complex property types) is more manageable in Oregon in comparison to let's say...California?

With high interest rates, there's less competition and more stable prices.

You can maintain a hands-on approach or enlist professional management services to streamline operations and maximize efficiency.Strategies for SuccessLocation Matters: Focus on neighborhoods with low vacancy rates, good schools, access to amenities, and proximity to employment centers.

Is it worth it for the interest rate to go significantly up to get the funds to help fix up current condo to rent it out, house hack another home and purchase a multi-family home?

Sufficient capital to fund the marketing campaign resulting in deal flow2.

Historically, residential US mortgage rates are near their long term averages.