Then I read Rich Dad, poor dad which completely changed my mindset.

I could have found the money I bet, but I was scared to be a landlord.

Hey @Mike Pepperday, AirBNB and VRBO are your best bet to see what kind of demand there is for STRs in general.

Mainly I’m trying to avoid “aged poorly design” glassblock walls, small bedrooms, older windows (wood/aluminum, single pane), aluminum patio covers, and to a lesser extent landscaping.

If you ask nicely and promise not to share, you can usually get good financial information on the properties that are currently operating as a STR.If you're just starting out looking, you may not be aware of just how many cabins out there are poor quality builds due to the lack of codes.

Your best bet is to read information from public blogs that approach both options objectively.

Or rental demand could be poor leading to higher than norm vacancies.

Poor lighting.

Here is a list of what adding ADUs, especially in single family zoned areas,  in my CA market is typically a poor RE investment:1) The value added by the ADU addition is often significantly less than the cost of adding the ADU.

Since Joe is not a registered lender, Joe is not held to the same standards as a lender and the sale could be a wreckless and poor activity by the bank putting Bob in that situation.