If you haven't checked the market for homes with "inlaw suites" or whatever your market equivalent is that can be a way to get it done as well. 

am working with them now and had the first policy (with Spinnaker) cancelled for nonpayment/late payment so we rewrote another policy (with Millenial) and having the same payment problem again but at least they are communicating that cancellation is coming. they want me to pay by credit card over the phone so the payment wont be late and cancelled again. but when i go to mycoverageinfo.com to check on status it shows its been paid.

Certain neighborhoods do not allow STR so be sure to check the restrictions when looking.

My friend @Miller McSwain has a ton of knowledge on Co-Living if you want to check out his stuff on how it works in CO

You will need to check with the city/building inspector to determine your options first.

Mine is a 2022 build  Hey Ryan, Your property checks alot of boxes for me for a MTR focused on attracting families as a whole home rental.Single story, Good school district, Little to no competition on Airbnb, No HOA.I bought a property once in 2015 and it barely cash flowed as a LTR but now 10 years later, I cash flow as a LTR about $600 per month. 

But I’d say if you check the spaces and everything passes the smell test, should be fine.

Appraiser will check the rent schedule and if there were any improvements done.4.

Yes this is possible.Go check with your original lender on the first property if you had one. 

Lots of posts on different companies so be sure to check out what people have said about vendors you are considering doing business with.