It really hasn't become a problem as I have gotten better and more efficient as time goes on.  

.: Well, actually it's a huge problem.

It’s definitely a strategy that works, plenty of Section 8 coaches will vouch here but it comes with its own set of problem.

@Richard Badamo you're welcome.The increase in tourism is no cure for the problem, as it brings more supply and more competition.

I spoke with someone from Asset Based Lending about obtaining financing, but was told that the commercial zoning is a problem as they don't do commercial loans unless it is multi-family. 

Same problem as above.

This will translate to them charging what may seem like a lot of money for a small problem, as the chances of having to deal with a problem for an extended period of time are real from that point on.That being said, if the other landlord is being unreasonable and requires a contractor to do the work, you may not really have a work-around.

A bad tenant is ones worst nightmare, especially on your first rental.SO I see the problem as not vetting the property, and not vetting the tenant.

Is the problem a lack of lenders or is there a problem with you as a borrower?

This is my first year running an STR, and I ran into this problem a few times over the summer.