Investing in real estate would be a lot better experience if people educated themselves on how to properly manage from the very beginning.

Sounds like for now the idea of eventually selling the branded account is a no-go, but there still remains pros/cons on each option and I'd love to hear what others have considered or their experience in adding more STRs/boutique hotel type properties to their portfolios.

My experience with S8: There is a reasonably strong correlation between S8 tenants and tenants that do not take care of a rental property. 

So I am not telling you what do, rather I am just sharing my experience. 

In our still relatively limited experience, seller financiers are usually looking to get a higher asking price in exchange for the favor of the private loan. 

We have 20 years of experience and are always looking for investors to work with. 

Coming from a family of lawyers the ones in my experience that make less than that are usually just not that motivated or are not that good at what they do.  

@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. 

You’ve gained valuable experience from your first duplex and are now approaching real estate with a strategic mindset

No complaints at all.MathewHi Mathew - just checking how was your experience with them ?