Over that time we have acquired 4 properties, 6 doors. 

This will save you time and effort, as you won’t have to travel long distances to manage different properties or handle tenant issues.For your first investment, I suggest starting with 2-4 unit properties.

He speculatively questioned,at that time, "What will these look like in 20 years?"

Like everything in real estate, it comes down to negotiating a good deal upfront.

My problem: I’m having a hard time picking a market that meets my goals.

@Joseph FennerThis question has come up from time to time.I use the app.

Another aspect that's important is to communicate to your relinquishing property buyer (Boston condo) that you're going be doing a 1031X and that they can offer you flexible closing time.

The stock market, gold, Bitcoin, and most real estate are all at all-time highs.

It will take time.3) Property management companies, chamber of commerce meetings, local commercial RE brokers, etc are all additional options to network and find people who do deals.

I am considering the pros/cons of doing this without a property manager or real estate agent.