Don't settle for properties that merely break even; aim for those that generate consistent income from the start.

I'd look at land development as an equity capture tool to generate additional returns. land is a buyer's market in almost every market. you just have to expand what you are willing to do or your strategies.

Could long distance investing fit into your time and energy resources?

If you want to generate wealth over time, then it is a good thing to do.If you want to generate money for flight school I would look into doing resale on ebay or something similar

I am a strong proponent of what I refer to as proactive asset protection but its not promoted because its not the revenue generator that other asset protection services yield.

By renting out both of our properties, we will generate enough income to cover the rent of our new home.  

Generate at least 5 rental inquiries per week.3.

Multifamily properties are a fantastic way to start, especially for building a solid portfolio and generating consistent cash flow.Madison and Milwaukee are great places to look at - they have very robust rental markets and economic stability.

Keep in mind, I'm a long-term rental operator and hold (typically) for a generation or more. 

Quote from @January Johnson:Yes, cash flow is hard to come by but STR management is certainly a full service offering and requires a good amount of time, energy and care to be done right.