And the locals in Highlands have been fiercely debating STR's and regulations for the last few years, so I wouldn't be comfortable buying there.

Quote from @Jimmy Chao: I am weighing some options to help my younger brother buying his first primary with a fixer.

Say they sold the properties over 3 year period and could not sell the rentals together as a portfolio.Could they put the money from each sale into a DST then use the total to buy a expensive rental property?

It will be even harder as a young person with no life experience, and particularly no experience buying real estate. 

Buying now means investing in a market that appreciates at a steady, reliable pace.

The secret is deploying an unfair advantage and/or buying good assets + time.

You are generally going to either buy it at 95% of value or what is owed, which ever is lower. 

Some 'ting fishy and smell of foul odor.ARV of $375,000 and buying for $103,000?

Get a 50% LTV loan and buy another property just like the one you own. 

They will see a large pipeline of local deals, and they will buy some as rentals, flip others, and flip the contract (wholesale) a handful where it makes sense.