Off street parking is typically more important for high end/expensive rentals.

Regardless of if there is a due on sale clause or not - if you are paying a 2% of property value tax twice - that's a large expense.

I understand why it is extremely expensive down there too.

I wasn’t prepared to lose so much of my savings as carrying cost basically I paid for the tenants to live there for 3 months + my own living expenses in that time.

After every negotiation, reflect on what went well and what could be improved.Negotiation isn’t about “winning” at the expense of the other party—it’s about finding common ground where both sides feel satisfied.

Any advice on expensive flips?

Our aim is to maximize appreciation and rent growth while still cash flowing enough to break even after all expenses in the short term.

(Maybe the seller has a great interest rate, but you would have to pay twice that amount which wouldn't be profitable.)11) Crime in the neighborhood. 12) High turnover in tenants (raising your expenses.)

As far as purchase price - I find older homes you can get a much better price on and rehab and still be slightly under market value - and the rent will support the mortgage and expenses.

We're looking to transfer this into an LLC for liability purposes.From what I can tell, the best way to do this is to retitle the property, pay Chicago's expensive retitling tax, and set up an operating agreement, all of which likely requires a real estate lawyer (what $ base do we use on the tax, given we aren't selling it to ourselves, just transferring it?).