I have basically 1) rewarded poor tenant behavior 2) tenant has no eviction on their record making it more challenging for a LL to determine that the tenant has been paid before and seeing it worked so well is likely to repeat the same $hit.  

Hey Jake,You'll definitely have some options with DSCR lenders, but you'll need to be really sure that the lender you use is okay with underwriting STR income as well as with the ADU as a mid-term as they are kind of tricky.With DSCR loans, your credit score is going to be a big determinate to where you will lend.

But no idea where to start or how to determine if something would be a good investment   Looking forward to learning!

Everybody says their projections are conservative :) It's up to you to determine if you agree.

Supply and DemandIn real estate, prices and rents are determined by the imbalance between the number of buyers and sellers.When there are more sellers than buyers, prices decline until there is a rough balance between the number of buyers and sellers.When the number of buyers exceeds the number of sellers, prices increase until there is a rough balance between the number of buyers and sellers.Rents follow prices.Higher prices reduce the number of people who can purchase, increasing demand for rental properties and increasing rents.Lower prices enable more people to purchase, decreasing demand for rental properties and decreasing rents.What determines demand?

I am eager to and determined to get to work.

I would say figure out your long-term financial goals and determine the best course of action with this money.

All these software will guide you on your declaration asking you basic questions to determine what you need to do and what not. 

Let's assume for a moment that townhomes are an approved use for your property, I would want to quickly determine the availablity of all necessary utilities to service the property.

Instantly I can tell the hottest markets from the normal and cold ones, and separately determine which one's I am priced out of due to crazy high values.I'd suggest a similar value-based approach if you have the data to calculate on to identify a few markets to start looking for deals in, but remember this is still too broad of analysis to make a go/no-go decision on the projects you find.