He was a realtor based in the Midwest (I think the greater Chicago area) and was talking about off vs. on market deals and the importance of choosing equity over cash flow. 

So, I think you have a risk factor in upstate New York that you don't get in most other areas (it's not where most people would choose to live).I think upstate New York one of the few areas in the country you can cash flow in B areas with 80% downpayment, so that's nice--in terms of deals, I think the numbers still work out at market prices.Finally, the property taxes are very high in upstate New York. 

Just make sure the market you choose aligns with your investment goals!

We recently switched all our properties to a commercial policy with larger umbrellas my question is:Do you have your residential properties insured under a Landlord policy or Commercial policy, if so what why did you choose that one?

Choosing a solution like that means missing out on significant opportunities to free up your time for what you do best while also foregoing the expertise of a tax professional who could provide substantial benefits—potentially saving you thousands of dollars.

@Rickey MayesCongrats on your condo purchase, Since it's your first home and potential rental, choosing the right mortgage and down payment is key.

If that tenant chooses not to pay the vacated tenant's rent for a month, that deposit can be used against the rent owed. 

Choose something modern and clean.

Good luck in whichever path you choose to follow!

First, you or your employee don't have the freedom to choose between 1099 and W2.