Financially, I’m not in a position where I need to rent it out immediately—I can afford to wait a bit if needed.This is my first time as a landlord, and I was lucky with my first tenant, who was fantastic.

You can tell when someone seems a little shady–when it feels like they’re not quite giving you the whole story.If I were considering a business to buy and everything looked fantastic on paper, but I wasn’t getting a good feeling from the seller, I’m not buying that business.Because as someone who has sold a business, I know there are things I could have hidden from my buyer.

My brokerage is part of Anywhere RE, we have the biggest names under our umbrella (ERA, Caldwell Banker, Sotherbys, BHG, Century 21) and we have a fantastic referral program that I can hand pick an agent anywhere in the country and interview them for you to make sure they have the qualities you are looking for.

And, none of them would want to be in all 3 cities unless it is a fantastic deal.

Section 8 tenants can be fantastic renters if screened properly.

It’s fantastic that you’re diving into real estate investing.. especially multifamily properties, which can be a powerful way to build wealth and generate consistent cash flow.

The Upper East Side is a fantastic area, and your budget gives you great options to consider.

For someone that's not as conservative, or a different view on the cycle, they might have a different opinion than me on all of this.2) Sponsor quality check: (takes about 45 minutes per deal)I believe that a great sponsor can take an average looking deal and make it great, and that in mediocre sponsor can take a fantastic looking deal and make it bad (especially if there is a severe recession).

Taking in the content sounds like a great starting point, and teaming up with someone experienced in these deals is a fantastic idea.

A tidy profit, plus confidence to tackle the next project solo.On the topic of self-directed IRAs: While they’re fantastic for gaining experience and diversifying into real estate over time, they can feel restrictive if your main goal is scaling quickly.Here’s what I’d focus on:Using Equity Wisely: A HELOC or cash-out refinance could unlock funds to pursue a flip or duplex without touching your 401(k).Partnering Smartly: Your realtor friend sounds like a great resource.