Just make sure you’re prepared to cover any shortfalls on that property and have a strong plan for deploying the new capital effectively.

This building needed new roofing.

Being clear about what’s covered in the lease and by local laws can avoid misunderstandings and set their realistic expectations.If you do plan to carry out the cosmetic upgrades (because the property is overdue and of course you want to ensure your tenants are enjoying their home to the best of your abilities), try to schedule the repairs at times that minimize disruption.

It helps cover your mortgage and gets you into real estate investing early.

We made to make some upgrades to cover the number of people but haven't had any issues other than normal maintenance yet. 

Renting it out now could help cover the mortgage, and you’d benefit from any appreciation over the next two years.

I cover utilities.

I’d prefer to avoid double-paying for insurance if possible.Additional Note: This property will be used as a short-term rental, which adds to the complexity.Any advice on how to structure the insurance to cover all bases without redundant costs would be greatly appreciated!

Since then, I increased my security deposit to cover more than a half month's rent should I need to use it.

When you have a tenant issue there aren't a bunch of other units to cover the shortfall.