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.

Not in all cases but more often then not.Additionally you have to have solid management who is checking on the property at a minimum once per quarter as many times I find these tenant don't always report issues timely.  

Also check into bylaws to see if you are allows a second freestanding dwelling on your property.

Go out to AirBNB and VRBO and check the area where you are looking.

Going to start by checking into local REÍ meetups and talking to some friends and family that are doing what I’d like to.

I use problems like this to go an check out the problem and then the entire property while I'm there, looking for other problems, but also assessing HOW the tenant is taking care of the property.  

My approach is to take a few minutes per quarter and make sure it is accurate by manually checking my true competition and adjustmenting prices accordingly. 

Quote from @Garrett Jennings: I wanted to check on the forums before I consider using this as a strategy.  

Hey Ryan I'd check on furnish finder or airdna to get estimates.

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