Does this payment make sense for my financial situation? 

There are other ways to finance your investment with a low down payment.

Referral fees are a "no-go" but you could possibly start up and run an advertising business to sell leads as long as payment cannot be tied back to the successful closing of a lead provided. 

You need to make sure you show 12 months cancelled checks or bank statements to show payment received.

If you do a cash out refi and choose to do an interest hold back there is no reserve asset requirement. 9 month of reserve payments will be used from cash out proceeds

This $8,000 would include your primary residence, HELOC payment once drawn, about $270 per month for forbearance student loans, and whatever the leftover monthly mortgage debt service is of your condo purchase after taking 75% of its monthly rent minus its mortgage payment.

Mid 700's credit, no cc debt, 1 car payment. 

When it comes to buying a 2-4 unit property with 5% down conventional, the guidelines mandate that you have 5% of your own funds being contributed towards the purchase to meet down payment requirement. 

Typically, we have seen lenders notice when the payments aren't made and then they go to see what remedies they have.  

We include common areas, backyard, front area, noise regulations, roof access regulations. late payments, fines for pet waste, garbage disposal etc.