We now live in Arizona and I frequently fly back to the southeast to repair or inspect the properties and already deduct the travel, lodging, and half of the meal expenses from my taxes. 

Hey All, I'll be traveling to Costa Rica for a wedding and wanted to explore the market while I'm visiting.

I am torn because I also like to travel, fish, backpack and making money takes some time. 

I travel somewhat frequently for work during the weeks so also trying to wrap my head around how to best structure for that.Anyone open to connecting and / or have any trusted people to help in the event of maintenance issues?

That could be a short term rental where people stay a couple nights at a time, someone coming to town for a work purpose for a few or several months at a time like a traveling nurse who signs a contract for several months. 

I would want to target corporate rentals, travelers, students.

Both Raleigh and Greensboro have their advantages, but with your experience in Greensboro and proximity to Cone Hospital, MTR (mid-term rentals) could be a strong option, especially for traveling nurses or medical professionals.

It is also worth noting that property management is often closer to 30% of gross rent for a short-term rental due to the much more intensive hands-on management compared to a typical 10% for long-term and as such, I agree with recommendations above that medium term rentals may provide the best of both worlds if you are able to tailor proximity to a local need, e.g. hospitals and travel nurses.Again, happy to relay my personal experiences in the area if you're interested.Best of luck,Patrick

It’s a high-risk strategy that is hard to pull off.That’s just investing remotely, which usually means traveling often to the market.

There are PM's that manage on that side, Kansas City property managers don't generally travel that far.