I got a Heloc to buy a piece of property at the first of the year, 5.99%.

We’ve always had the intention of cash out refinancing into another property once the time was right.  

Furthermore, they will pay the monthly rent to my company regardless of occupancy, so the 5K/month is assured.

Never had issues with filling the rental?

When a tenant signs a lease after 15th of the month should they pay the rent amount for the remaining days in the month or remaining days in the month + next month?

The key here is buying at a discount.

Since she is already willing to go to court I know she wont actually leave or pay rent but I want to make sure She cant say on court that she didnt pay because she didnt know how much to pay.2- On November 5th (because thats the date of the notice to vacate I put in because I thought I had to give her 30 days and I wanted to be nice) I will file for eviction.The issue is that I know the previous landlord used to pay the eletric for the house, though the lease clearly states is the tenants responsability.

Quote from @Ashton Rodgers: The last four years I've been successfully flipping land.

Hi Daniel Simplified also runs meetups in your neck of the woods. second Thursday of the month I believe they have on in Lowell. 

The fact that you have 3 separate leases does not make it a multifamily triplex.