I don't know if coaching will help or not.  

I'm starting to acquire furnishings and am looking for a checklist of sorts to help keep myself organized as I seek the best deals on high quality goods to furnish our rental. 

This helped me yesterday when someone inquired about a stay in October. 

I started this a little over 3 years ago now.I think thorough research, and data will help make educated decisions, and the real winner in this market is finding a mix of at least 2 of the four:  Off market discount, fixer upper, lowball on market offer, or seller financed/subto.Also if you are planning to do it in a populated area I also think its good to take on the idea of not cash flowing for a few years, and also considering air bnb if you want to reduce costs even more.

A knowledgeable attorney can help you set up compliant contracts, review your processes, and ensure you’re staying on the right side of the law.5.Consider Structuring Deals for Investors•If you want to avoid Dodd-Frank requirements entirely, you could focus on selling to investors or structuring deals for non-owner occupants.

A few chapters in, I can't help but wonder—do the strategies outlined in the book still hold up in today’s higher interest rate environment?

California's probate rules can be drastic in the event of death that having a proper estate plan in place can help in any number of situations, including if just traveling or incapacitated.These are all things you will want to discuss with your attorney and CPA.

You are considering putting a tiny home on your existing property as an ADU or using that money to save up and buy the next investment property and wondering which would be the wiser choice.I think ADUs can help provide additional, much needed, housing.

Could a return to independence help lower mortgage rates, or have other positive effects?

Chicagoland as a market may appreciate at different rates, and property taxes certainly do not help the cause.