Your next real estate competition might not be Black Rock or Bezos...it could be coming from the family of the friends you grew up with. 

But what really makes Reston Virginia such an interesting investment is the meteoric rise of the Reston Town Center, and its recent office market outperformance.

This would mainly depend on the market as you said.

You can find great 2-4 unit buildings at reasonable prices (compared to New York City), and many of them need to be fixed up, which is an added bonus of equity if you are willing to tackle a renovation.I'd suggest somewhere along the blue line (train) in the northwest part of the city, where you can find some priceless neighborhood vibes.Plus, the real estate community is unmatchable...tons of people willing to give you a hand up.

Maybe in a Market where housing is less expensive.

I don't have personal experience with this kind of land trust but since you're in CO I have a personal recommendation of a real estate attorney here in CO who has helped me with seller finance deals and is very responsive and has been great to work with in general - Jeromy Geraghty - https://www.geraghtylawoffice.com/

I'm quite fond of the market myself. 

The short term market is seasonal.

My company has discovered a niche and under valued market in Cape Breton, Nova Scotia.

Insurance is the most important thing as he said.I wouldn't make any decisions on this until I got with a solid real estate INVESTOR CPA.