Red flags (such as code violations etc) generate motivation, combined with equity generally lend themselves to producing deals.

Historically real estate investing does not produce an income to live on until you have built up a lot of equity.Some buy, fix, sell or other variations.

Later, after 10 years of rent increases, the units were producing $1,100 a month.

Even if the property was listed with an agent you would still need someone to produce most of the documents as an agent only gets involved with the purchase agreement.I do not understand the question concerning insurance.

Does MLIS advertisement produce better tenants?

We need to strike a balance with cost management strategies and ways to healthy living.

I would like to do this due to the income stream the second house would produce, but I am afraid that I would be over-leveraging myself.

I recently bought a property with 20% down and even with a HML in second position it would still produce a strong CF depending on the terms.

Don't forget eating healthy, family time and actually doing some fun activities.

BTW: What kind of annualized return are the 401K funds producing at this point?