Analysis paralysis. Help me decide where to invest!!

[Rita Oliva]

I'm a newbie. My husband and I have finally decided to buy our first investment property. He's leaving it up to me to find a place, and I'm afraid I'm slipping into "analysis paralysis" territory here. I know that once we start, no matter where we invest we will learn a ton and things will begin to snowball, but I'm having such a hard time knowing which option is the right one for a first timer. We live right outside of D.C. where prices are kind of obscene. Most of the areas nearby are either outside of our price range, or don't have much cash flow (although there's a good history of appreciation). So here are the options we're considering: 1. Invest nearby in a 1-2br condo. A/B neighborhood. Cashflow would be breakeven for a standard rental or 200-300 a month for vacation rental. (60k 25% downpayment) 2. Invest in a single family slightly further away in Maryland in a transitioning C (maybe D) class neighborhood. Rental cash flow around 200 a month. (40k 25% downpayment) 3. Buy a SFH in my hometown in FL in an A/B neighborhood. Cashflow 200 a month but lower price point and solid appreciation. (30k -40k 25% downpayment) 4. Buy a townhome in my hometown in FL in a B/student housing neighborhood. 250 a month standard rental cashflow or potential 500 a month Vacation rental cashflow. ( $20k downpayment) 5. Buy a duplex or multi family in my hometown in a D neighborhood. $500-600 cashflow but no appreciation. ($40k cash and $4k rehab) 6. Buy a 4 unit multifamily in my hometown in a C neighborhood. 700-900 cash flow. ($40k downpayment and $5k rehab). So, the question is, do I go for something that will extend me a bit financially with possible long-term gains close by, something safer with lower but solid return that's out of town, or "go big" for high cashflow in a riskier area out of town? Also to consider - if I went with the out of town option I would definitely get a property manager. Also, most of the properties in considering out of town are already tenant occupied. I have family in my hometown who would be a local point of contact, and I typically visit 1-2 times a year. I'd love to hear your thoughts and input!