My buddy just invested in Akron Ohio long distance from NY.

If you end up picking Westchester and north, make sure you're not too far away from an Amtrak and/or Metro North station as those are crucial for people commuting into the city. 

We want to sell to transition to STR and also invest more locally as long-distance investing comes with its challenges.Does anyone have advice on how to get the best offer without lowering the price further?

On my schedule is to start identifying and researching the top RE pros (Agents, Brokers, Investors, Property Managers) here at home and in the markets within a driving distance (Huntington WV, Lexington KY, Columbus OH, and Charleston WV) and start weekend visits just to drive around.

It can be done with FHA loans, short-term rentals (Airbnb), long-distance landlording, live-in flips, or partnering with family.

You can still self-manage from distance and utilize help when needed for the local tasks.

I know this thread is a bit older, but wondering if anyone is still finding success in Iowa and would be willing to connect for some advice in the long distance SFH rental market. 

Pete aren't highly rated so targeting families at a higher price point for single family homes doesn't seem possible to me at the moment since these house are more expensive and most families will commute to private, charter or magnet schools so location doesn't mean as much.

Being 1.5hrs of NYC gives you a lot of options, even Long Island (which typically has more options for public commute into NYC).Give me a shout if you'd like to chat more, I have a handful of case studies on my site as well from deals I've closed/brokered that match the househacking criteria you're aiming for. 

Americans couldn't own land a certain distance to the beach when we owned there.