I'm sure it was highway robbery - it certainly was based on the man-hours it took - but when you are in a desperate situation, you do what you have to do to get yourself out of it.  

Then rent the bigger home out using a property manager, allowing her to possibly cash flow and maintain that asset and let it continue to grow in value.Encourage her to consult with a CPA or tax attorney to explore the best strategy tailored to her situation.

I think I'm in a pretty unique situation and am trying to figure out the right hoops to jump through to move forward.Long story short, I'm trying to tap into the equity of the rental property passed down from my grandparents that is held in an S-corp which is co-owned by myself, my siblings, our cousins, and an idiot uncle.

If you are just getting started here in Chicago, house hacking is the ideal situation.

Sometimes the asking price does not reflect what's actually going on, there's a tenant, there's a change in the seller's situation, etc. 

My concern with declining values, increased inventory and a weaker economy would lower rental income and could potentially put me into a negative cash flow situation.

Just depends on the situation/scenario.

In 2019 I purchased a Duplex in New Orleans for $219,000, I was able to refinance during Covid to a 3% interest rate. After I left NOLA, I was able to rent each side for $1,295 through a property manager taking 10%. T...

Since this is the tenant's money, I want the bank calculating and holding everything versus storing balances in my spreadsheet.

LTRs do not face those types of situations.