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.

It's a bit old school but the price is reasonable. there're better systems out there but you pay for the premium. 

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

They have mortgage insurance premiums, while with conventional loans you will need to pay PMI until 20% in equity.

If you choose a Direct Premium subscription with Hospitable, you get $5M worth of damage protection (powered by Superhog) on every booking2.

My premiums on my properties are ridiculous.

Pros:Potential for Bargains: Auctions can offer properties at lower prices than traditional listings.Speed: The auction process is usually quicker than traditional sales, with a defined timeline for closing.Transparency: The bidding process is transparent, and you can see competing bids in real-time.Cons:As-Is Condition: Properties are often sold "as-is," meaning no repairs or warranties.Limited Inspection: There may be limited opportunities to inspect the property before bidding.Financing Challenges: Securing financing for auction properties can be more challenging and may require quick approval.Auction Fees: Be aware of any additional fees, such as a buyer's premium, that could affect the total cost.I hope this helps you out!

Other features include, LED lighting, new ceiling fans, updated laundry room, privacy fence, and new landscaping!

They have this feature where the investors’ accreditation status verification is automated.

Very similar to what you're forecasting, although it seems like you're adding nicer features.