@Kevin Connauton, I agree with you that although Pad Split is a great choice for getting the rooms filled, they don't cover all your bases in terms of property management.

Aloha Joshua,  I deal with clouded/messy titles often and it's not my first choice as its froth with a lot of time, costs and risks. 

In the long run, I want to have properties that are producing strong cash flow (eventually would love to own small apartment buildings and syndicate larger deals), but it seems that focusing on cash flow and reinvesting those cash flows will be a slower process than focusing on properties prime for appreciation or with opportunities for forced appreciation.

With a larger organization like iintoo you'll likely be talking to an account manager that has been assigned to working with you.

Since you won't be able to recognize it as a valid rental if you're charging under market rent and you also expect to be covering any house expenses that are outside of her budget, this seems the best choice. 

These deals typically require larger cash outlays (50k-100k) per deal minimums.

I really want to start my investment journey but I'm not sure if an out of state property would be a good choice while renting in NYC or if we don't move, to move to a cheap market, live in the property for a bit and then rent it out.

Your real estate happens to be a % of the larger piece. 

My wife and I have a vacant lot in Tallahassee and we're looking to use the current equity to exchange for a larger single family investment property.

I think a good starting point would be looking at the comps in your area (recently renovated or new construction homes) that sold around your desired sale price and in your desired timeframe and taking inspiration from there design choices.