But my fear is using my funds in down payments then losing momentum until I have more saved up to do it again.

I find that one of the main fears holding people back from starting their investment journey is "lack of money."

We're looking into house hacking as a way to start, but we fear it might be too slow of a burn starting at age 29 that might not pay off in the end, especially since we don't want to live in a duplex forever...we have to get out of it somewhere, somehow.At $3600/year, it sounds totally unfeasible to do anything beyond our brokerage $500/month investment as any sort of savings for anything, whether benefitting the house or possible future expenditures and this has been bothering my mind for awhile now and created a lot of stress involved with the house. 

What's strange is that there is no other option in that area with such competitive prices and high quality, we have even though that many people might even be reluctant to inquiry about the lots fearing that they might be too expensive.

Investment property contract period is different then when I bought my single family home.Challenges is dealing with the fear of missing something big.Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Buffett to consider as we apply them to real estate investing:“Our goal is more modest: we simply attempt to be fearful when others are greedy and greedy when others are fearful.”This aphorism is a natural for those of us with an inherent contrarian attitude.

We fear that we could move away, outsource to a PM company, and come back in 3-5 years with properties that seem neglected or run down, or simply not managed anywhere near the quality standards that we maintain today.

Investor had multiple properties, multiple businesses, multiple bank accounts, and feared multiple lawsuits over at least 3 continents.)Buyer wants to be invisible.

Don't fall into analysis paralysis and afraid to take the leap for fear of failure.

Period.It doesn't matter that I learned the apartment investing business, made industry connections, got over my fear of making cold calls, or hired & trained my team to skip trace and make calls for me.Pure "Mamba Mentality".