From my understanding if he gets hurt on the job it would just add a layer of protection for the landlord. 

Credit check, income check, debt to income check, possibly requiring a co-signer as well to ad an other layer of protection.

to start: large level and small level power tools (drill, saws, nail gun, multi tool) screw drivershammersmeasuring tapesstud locatorchalk stringpry barvicesmagnet wire stripper flashlight tapes (duct, blue, masking)paint brushes, rollers, pans gloves putty knifestraight edge cutting tool steel woolpapertowels, shop towels  garbage bagsmagic eraser

@Shane DuncanIf you have any friends in the business you can pass capital through them to create an added layer of separation as well.

Selling now means you could miss out on potential future gains.Market conditions: If the market is currently down, you might not get as much for the property as you would in a stronger market.Option 2: Get a Loan to Fix the BasementPros:Increase property value: Renovating the basement can add significant value to your property, both in terms of rental income and resale value.Higher rental income: With the basement fixed, you can charge market value rent, which could help cover the mortgage, property taxes, and the cost of the loan, with the profit potential.Tax deductions: The cost of renovations can often be deducted from your taxes, either through depreciation or as an immediate expense, depending on the nature of the renovation.Cons:Additional debt: Taking out a loan adds another layer of financial obligation and risk, especially if the increased rent doesn't cover the loan payments.Renovation risks: Renovations can sometimes uncover more issues that need fixing, leading to cost overruns and delays.Market risks: There's no guarantee that the market rent will remain high or that you will find tenants willing to pay the increased rent.Additional Considerations:Current Market Analysis: Understanding the current real estate market in your area is crucial.

Finding one that has built in padding and a thick wear layer (10 or 12 mm) makes for easier install, it holds up forever, and is just all around better. 

I would agree with the other Derek here that high leverage especially on your primary could have some extra layers of risk. 

It was a wood composite with a vinyl top layer with texture.

Not only do I need to perform somewhat similar tasks as an agent, I need to perform wholesaling duties, which is another layer of tasks.

If its a shingled roof ask whether it can be a rollover roof (just adding a 2nd layer of shingles) to reduce the cost.