The tourism authority has had some good information in the past about how many visitors come to each island and, of those visitors, how many book STRs.

In my case, I reimbursed half the locksmith bill, similar to what you offered, because while I felt responsible for not having a spare key, I thought the tenant should also share some accountability for not checking with me before authorizing additional work.If this situation happens again, you might want to build specific guidelines into your lease about contacting you before any repairs or services are authorized.

The rules and payment standards vary significantly from one area to another, so familiarizing yourself with the local housing authority's procedures is key.

I don't have much experience dealing with Section 8 and I wonder whether there's a risk of bringing attention to a non-conforming rental to the Section 8 authorities. 

What I have seen in the research is to find a property you are interested in and compare to other comps in the same neighborhood.

My realtor told me that there's been happenings of neighbors turning in people who are doing STR's and getting investigated by authorities, resulting in fines & such.  

Just be sure to clarify that she isn’t a leaseholder but is authorized to reside in the unit.If you’re concerned about liability or want more peace of mind, you could ask the primary applicant for additional security, such as a higher deposit, depending on what’s allowed under Colorado law. 

To minimize delays, it is important that you get approval to be a section 8 landlord from each housing authority.

This is from personal experience, the housing authority is the problem.

I'm quite new as an investor, but with three books by Biggerpockets authors under my belt and plenty of enthusiasm, I'm ready to keep learning and to connect with like-minded people in my area and beyond.