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.

Then, when I found something that made sense pull the trigger.

This may impact the opportunity for winter STR there so take that into consideration.

As a listing agent, I let my seller know it can trigger the due on sale clause and they lose control of the home but still responsible for the mortgage if buyer doesn’t pay, so most aren’t interested unless it’s a special situation where they really need out and no real buyers out there.

We plan to consult a tax professional but I wanted some general thoughts and considerations prior to that meeting.

Don't know honestly which of those could be considerable renovations

Primarily with creative terms but also general strength of buyer position has resulted in considerable discounts or investor incentives particularly with transactions involving healthy cash portions of 1031 Exchanges. 

For comparison:10-yard dumpster: Holds approximately 3-4 pickup truck loads.20-yard dumpster: Holds approximately 6-8 pickup truck loads.Depending on how much debris you estimate (6 doors, carpet, flooring, old trim), an 11-yard dumpster might be sufficient.Cost Considerations: Dumpster rental costs can vary widely based on location, duration of rental, and the company you choose. $400 for a 2-day rental of an 11-yard dumpster might seem high, but it’s important to consider what’s included (delivery, pickup, disposal fees) and whether there are any weight limits.Alternative Options:Bagster Bags: These are large, disposable bags that you fill with debris and arrange for pickup.Junk Removal Services: Some companies specialize in hauling away specific types of debris.

As consideration for the loan we are providing and to secure your obligations under this Agreement, you hereby grant to us a security interest in the following property (collectively “Collateral”):all consideration received from the collection, sale or other disposition of the Collateralized Goods, including any payment received from any insurer arising from any loss, damage or destruction of any Collateralized Goods and any other payment received as a result of possessing any Collateralized Goods, or any other proceeds of Collateralized Goods."

Securing the necessary funds for rehabbing a fixer-upper for your future primary residence can be done through several methods, each with its own advantages and considerations.