Didn't quit the day job and don't plan to but plan on acquiring slightly newer product to prevent some of these issues.

Or are there ways to prevent this?

There's nothing preventing you from looking at replacements properties prior to closing on the property you're selling, You can even be under contract before you even close on your relinquished property.

@Basit Siddiqi true. the other side of the coin is with rehab situations sometimes there are issues with the property that prevent lenders from getting involved.

The 4th Thursday of every month is a standing inspection for fire prevention to check all smoke detectors and CO detectors.

Me personally will never vote for someone who prevented a peaceful transition because his ego could not take that he lost.  

Finally, make sure that your short-term rental (STR) meets IRS requirements and doesn't get classified as long-term or this could prevent you from leveraging this tax strategy event though you are materially participating in property and it was placed in service.

If I paid down 80% of the loan then obtained a 2nd position Heloc, is there anything to prevent me from paying off the 20% remainder on the first lien, then paying myself back the 80%, essentially leaving me with a first position Heloc?

I typically find a new tenant before they leave, or shortly after their leave, which prevents me from any losses and puts more money in my pocket.

Hi Everyone,     I am aware Colorado law prevents landlords from charging the tenant's security deposit for the time the landlord spends on repairs (though they can charge materials).