Why will your rent be LESS per month after the tenants move out and you fix everything up?

We should be closing by the end of the month and the tenant is already in place.

I do have monthly mortgages to be paid and not having rental income to offset my negative cash flow has been a learning experience and really trying to think of what options I have to have better success at this.

You will be doing more work on them on a daily and monthly standpoint, but overall..

Lenders will want to see those funds deposited in a bank or other lending institution on one or two monthly statements.

The second company had a PM contract and due to other reasons we did not continue their services after a couple of months so tax stuff did not arise.

Install cameras around the parameter of the property today; post no trespass signs; change your for rent listing. 

I let the booking expire and figured it was a troll.I then get another request from the same person about a month later for the same dates.

The guests stayed for a month and did not monitor this activity. 

In the end, it would have made more sense to hire a couple handymen for a week or two than me spending 3 weeks installing flooring, base and case.