I wanted to ask advice of some of you who have a lot of experience in long-term rentals. 

@Emily Gowen so as you pointed out you would not have to do a 1031 exchange on your current home to avoid the capital gains tax and coupled with what Dave Foster pointed out I think, speaking from experience you would have a high likelihood of success. 

Is the property just a regular-style house or something you can build an experience around?  

Most look at a Certificate of Insurance and confirm coverage limits but best practices are to (1) become added as additional insured under contractors policy and (2) understand coverage exclusions which are not going to be detailed on an insurance certificate.

I'd love to hear your thoughts and experiences!

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Dramatic experience for both our tenants and us.  

I would try to tie those experiences and skill sets to your REI path.  

These are professionals with additional training and a stricter code of ethics.

Buyers usually want to purchase on today’s value while sellers often want to use future potential of the property (“current rents are below market” or “room to build an additional property”, etc) to increase the purchase price or likelihood of a sale.