The area is more rural, however it’s a desirable vacation destination and we offer a high end farmhouse retreat experience.

Had our son in high school help out landscaping, running skidsteer, putting up signage, clean out units, run software, etc.  

For most of us, it's a math exercise. 

Also, planning to use the other side of the unit as short term rental.Any advise which could make this more seamless would be highly appreciated!! 

If you are interested in investing out of state I highly recommend that you build a strong team in your chosen location.

To help in your search:be sure to find an accountant who is willing to grow with you, and is not too high priced fee-wise.

Start complaining and take it as high up as you need to go until these brokerages take you seriously. 

As this would be in NYC the price point is very high so it makes a massive difference.

In the recent transactions Iv dealt with high rises Iv seen many special assessments in place for reconstruction of elevators and other contributing factors.

This strategy is great, but it fluctuates depending on the time of year, you probably won't live for free because it is more challenging since you are only Airbnbing a small space or basement unit.4) MTR - this is a good in between style of creative strategies since you can furnish a place nicely that would rent out on Airbnb but you want a long-term high quality tenant like a travel nurse or corporate rental that stay for 2-3 months vs. under 30 days for most Airbnbs.Combining strategies is the best way to go, ideally, you would find a property with a separate entrance or walkout basement, live upstairs in the one of the bedrooms, rent out the other upstairs rooms and STR/MTR/LTR the bottom unit.