When you move all of your insurance under one insurer, they can also bid down your individual policies to help save you money.

If interest rates settle down and rents improve I may try the Long term route.   

You're also going to need survey and engineering work to get the permits done for putting in the utilities to the buildings, flatwork and other improvement requirements around the buildings.

Does it improve the roof itself, or does it bring increased maintenance.

Are utilities paid by individual unit tenants?

Many investors make the mistake of over-improving their purchases in Class C/D areas, which when damaged by Class C/D S8 tenants - costs them thousands.Another fallacy of S8 investing is that the S8 Caseworker will keep the S8 tenant inline by threatening to take their voucher away.- The reality is this depends on each individual caseworker.

Use individual leases to reduce risk, screen tenants carefully, and set clear rules about noise and responsibilities.Good luck!

I’m here to network with like-minded individuals, share experiences, and grow my knowledge in real estate investing.

The type of your business or the fact that you are paying them as an individual does not take away the requirement to file 1099s." 

Start with your primary, rent out any spare bedrooms "house hack"Use that to practice upgrades, kitchen, bathroom, curb appeal... etcNow you have experience as a landlord and flipper, use that to buy a distressed propertyAdd 40% equity to the property through home makeover, refinance into a low cost mortgageNow you are cashflowing a healthy margin on a second property, use that to build equity over time, cashout later and buy your duplex/quad.If it's going to take you 10 years to save up a down payment for a small apartment building, yeah it makes more sense to start growing your portfolio with cheap SFR flips instead.Every market is different, every borrower is different, every property is different, it would be ill-advised to recommend anything without recognizing the individual's nuanced goals and objectives with their next acquisition.