Get a hold of a trusted lender and run through the options with them as well.

I had some success in doing a house hack short term rental with my first property and wanted to continue growing my portfolio.

A handyman may charge a minimum fee of $50–$100 for small jobs.

Also, first time working with a private money lender.

This is a story from my past that provides a perfect example as to why investing in tax liens at auction is so dangerous for any but the most experienced and knowledgable investors20 years ago I purchased a SFR as a long term rental investment that sat on a double lot.  

Airbnb hosts have the ability to make a difference.

You should talk to a lawyer.

They usually have a process for filing a claim with the city for damage caused by them, and they may be willing to cover it.

You'll need a solid proforma and to build a team with expertise.

I am a W2 employee.