I think these are mostly mindset issues and can be overcome with changing your thought patterns.

In any event I would assume a prorated amount would be the charge vs 100%.[1] How did you do that to them, because it looks like renter damage vs (wear and tear) to tops that will last longer then 15 years, (are these cigarette burns that you sanded down to try to blend into the busy pattern)?

Along with good work history and income, confirming this with bank statements and tax returns.Your observation is fair especially when it is 5 years ago, and the pattern stopped.

I am starting to see a pattern here :-) Thank you for your perspective on this!

And each of them follow a similar pattern.

I have been showing new homes to clients for the past few weeks and nearly everyone has a high quality LVP in some type of wood look alike pattern.  

Look for:Close - within a half mile, ideally.Closed - actual closed sales, listing prices aren't good data points.Comparable - similar bedroom count, both with and without an ADU (b/c that's what you're trying to research).Recent - the more recent the sale, the more relevant the data point.So you look at your two lists, spot patterns, find the median, compare the two median sales prices, and boom that's a solid ballpark.If you want to look at "Do I build a studio ADU or a 1br ADU?"

Keep talking to as many people you can until you see some patterns and can make an educated decision.  

With your fact pattern (purchase one unlevered property), I would look into converting the traditional 401k to a Roth (depending on the size of the 401k and your tax situation in that year) and investing the combined Roth in the rental property. 

Far more common for private mortgages such as this, but something to also keep in mind if you invest in mortgages and promissory notes.There are always outlier fact patterns, but a judgment creditor is not going to be able to jump priority like that in most cases and states.Contracts for Deed and Land Contracts generally are most favorable to the seller in most states.