Plus, the potential tenant will appreciate and pay more for a new home rather than an older home.

Quote from @Michael Ancona: Research all the it's and out's of DSTs before purchase Yes and I highlight the potential risks here. https://www.biggerpockets.com/member-blogs/7993/73161-what-a...In my firm, we underwrite the Sponsor as a company in addition to their individual offerings.

Now, if i raise it a little bit more, I get vaulted ceiling (more potential resale value + another rental with a tall loft style bed ) 

It's pretty straight forward to analyze the potential if other STRs are nearby.Did into your Airdna.co data and see how the best performers are doing.Let me know if you need help.Best to you

Your network is the most important piece for any potential returns when you invest out of state.  

This will cost thousands more to complete and loose many potential buyers . i have started the process for a land survey.

Me and my team would certainly be open to a quick consult to talk through your goals further and help unpack some potential additional approaches you may not have considered.Congrats on the recent acquisition!

The first property was a long term investment but I have a lot more flexibility now and am strongly considering moving there to house hack and potentially start building a portfolio.

I would also argue that there are plenty of landlords out there that have rentals which are currently below market rental price.I assume that this part of the tax code was created to prevent those with multiple homes from letting relatives live in one for almost free, while potentially hiding that rental income and not having it registered as a business and pocketing the money.  

After a while you learn the area and values and can easily spot a good value but for the most part we ignore the asking prices and send offers that make sense for OUR numbers and goals.We have to send a lot of offers yes but it ensures we don’t overpay or if we do pay full price it’s because we absolutely loved the asset and see growth potential.