In NH/NE, having a solid RE attorney who understands entity structuring and estate planning will be a huge asset — a lot of investors here recommend asking your CPA for referrals since they often work closely with attorneys.As for pivoting with purpose, many investors in your shoes start by clarifying whether they want to optimize for cash flow, appreciation, or lifestyle flexibility — that decision usually shapes whether they lean toward multifamily, short-term rentals, or commercial.

It's the lifestyle of doing what you want, when you want but also to scale up to a major player in the field.

The reasons why I really want to get into this: it feels like something that would fit my work from home lifestyle that I have established (I'm never going back to the office and even if this job ends I can get other remote project management that will also be work from home); I get paid 4 ways (W-2, appreciation, tax write offs, ownership distributions). 

However, if you are expecting this property to make a substantial difference to your lifestyle n the near term, I fear you are likely to be disappointed.good luck

I am an Executive in a life sciences company which takes the majority of my time and I have no intention of stopping that, but want to build a larger rental portfolio to have other financial / lifestyle options in 10 years. 

If I had to choose, I’d lean toward appreciation and long-term stability over maximum cash flow, but ideally I’d find a combination of both.For lifestyle reasons, I’d love to be as close to Scottsdale as possible.

That’s such an inspiring journey—you’ve really carved your own path and it’s awesome to see how you blended real estate with lifestyle freedom.

Quote from @Jacob Borstad: @Drew Sygit currently we have an emergency fund with enough reserve for a year for our lifestyle.

If the Tenant Buyer walks away from the deal I get to keep his Option payment, since it is non-refundable and I sell to another Tenant Buyer and get another Option Payment usually about $20k to $25k.I encourage buyers to get qualified for financing, give them a mortgage broker contact and to plan their lifestyle to be able to get a loan to exercise the Option.

If the STR makes sense for you and your lifestyle, then do it .