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). 

Obviously that doesn't fit everyone's lifestyle, but an extreme example of wealth building.

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.

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

Hey Evan, solid list of markets you’re looking at...those all have pretty different strengths depending on your goals.I work with investors in a few of those areas (Arizona and Texas especially), and what I’ve seen is people usually narrow down their choice by looking at three things:What kind of tenant base they’re comfortable serving (workforce housing vs lifestyle renters)Property taxes and insurance costs (big swings between states)How involved they plan to be in the management sideIf you’re still figuring out what kind of market fits your investing style, I can connect you with a few people who started out-of-state and built small portfolios in those same regions.

But about three years ago, after getting tenant calls on Christmas Day and again the day after, I did a lifestyle check.

But for the next year, we really need to be budget conscious as the previous management company threw money away (it truly is astonishing).