If your manager is just 'keeping an eye' on things, collecting/reminding on a few rents here and there and some light cleanup while being compensated in free or reduced space rent then classifying them as 1099 subcontractor is great. 

Here’s my two cents:Paying off the condo might make sense if your main goal is to reduce risk and enjoy the peace of mind that comes with no mortgage.

Options like a unique amortization schedule or a 3/2/1 or 2/1 stepdown interest rate could provide initial relief to get you through the renovation phase while giving the seller confidence in a structured payoff plan.To determine an entry point, consider reducing the price based on the current NOI.

Day 7: "Here’s a case study showing how we helped [Client Name] reduce costs by [X%]."

You'll likely also reduce your cost of living by moving to a stabilized apartment.Depending on the cashflow and debt paydown, you can use this strategy until you've built enough equity to reinvest.On the other hand, getting into a multi-family after refinancing will also help you build substantial equity to rinse and repeat in the coming years.

You could also add cash to your exchange account to reduce the debt replacement if you wanted. 

We also tell them that we charge $25 per hole for TV mounts, shelves etc I think that $10 up-front investment has reduced the number of issues by probably 80%.Our walls are textured (sand textured in Milwaukee, orange peel textured in the western suburbs - yes, there is an actual dividing line), so we try to avoid the usual palm-sized patch and fill only the hole without making it bigger, so we can get away without texturing.

@Will Almand A cost segregation (cost seg) study can accelerate depreciation on your properties, reducing taxable income by reclassifying components (e.g., appliances, HVAC) into shorter-lived categories.

This needs to be limited and reduced. 

We are definitely likely going to see a drop in interest rates, which means you could always refinance in the future too to further reduce your monthly payments.