To rent the home, I would lose about $2,500 per month (based on comparable rents in my area, property management fees, etc).Both options loose the same amount by roughly 2 years, and by this time, I still will not have built up much more equity in the home to make selling it a break even unless there is price appreciation by then.My dilemma is this: I speculate that my home will not appreciate much in the next 3-5 years due to the rapid pace of development in the surrounding area.In 5-10+ years, maybe, but by then I'll have bled $150,000 - $300,000.I have thought about this a lot and feel that I mar'-too close to the problem to see the best solution.

Thanks for your kind words and thoughtful insights.

Our initial thoughts have been to look up in New Hampshire, specifically the Lakes Region or up near Conway.

I have so many questions though.1) Can anyone tell me more about series LLC and whether it's necessary to hold each property in a separate LLC2) What are your thoughts on a trust, rather than an LLC - advantages, disadvantages etc?

@Nate McCarthy I think this could be a great opportunity if approached thoughtfully.

Any thoughts and feedback would be most helpful.  

If you invest in RE, whether active or passive(management team, syndications, crowdfunding), I'd love the chance to quickly explain the structure and hear your thoughts on what might need to be improved.

@Michael K Gallagher:Thanks for your thoughts!!

Am wanting to add a STR to my portfolio and thought having one near where I live was a better idea than investing out of state.

Thoughts on this?