You enter it as a monthly expense. 

. $1300/month, tenant pays all utilities. 4 bedroom one is vacant.

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..

Months later, Tenant is now claiming close to 10K.

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.

Unfortunately, the HOA prohibits leasing for less than six months.2.

Holding this for 1 month (hoping that's enough to refi) that's $5k.So my aim is to save money overall by making a cash offer and close it soon.

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).