I’m looking to earn some real money on the side (10-20 hours a week), ideally real Estate related but not limited to that.

Ideally I would balance them with both properties and have short-term during the peak season and midterm through the winter.

As a buy and hold guy I am looking for greater security than a wholesaler or flipper might have seeing as they are going to get out of the property, ideally before it floods, and I want to have the home kept nice and safe and dry for a long while.

Ideally, I'd like for my wife to transition over full time to our REI business first, then I would like to follow suit within 5 years or so.Looking forward to networking and learning with some of the best here on BP!

Not ideal for a flip

Second Is What would be your ideal outcome from the situation?

I am located northeast of Houston and so would ideally like to find a deal in the north/northeast portion of Houston.

I'm interested in getting into flipping low-mid priced homes in the charlotte area, and ideally find some buy and hold opportunities for the long term.Im working on becoming familiar with the city and it's small "pockets" of diverse neighborhoods and hoping to meet and discuss the area and business with other investors, RE agents, contractors, etc to hopefully do business with down the road. 

Ideally, you want several employers to spread the risk associated with a dominant industrySupply and DemandCensus.gov under the “Selected Housing Characteristics” tableDetermine by analyzing the five-year rental vacancy rates and median rental rates in the market, as well as the year-on-year change in the number of building permits created for commercial properties (five or more units)The number of five or more unit building permits won’t tell us much on it’s own.However, a huge red flag to you would be when you see an increase in the number of permits in combination with an increasing vacancy rate and/or a decrease in median rentsAs vacancy increases, median rent and new building permits should decrease… and vice versaBest Case:Low or decreasing vacancy rates and increasing median rentsDecent Case:High vacancy rate that is decreasing Stagnant vacancy rateWorst Case:Increasing vacancy rate and/or decreasing median rent An increase in the number of building permits (5+ units) in combination with an increasing vacancy rate and/or a decrease in median rentsMiscellaneousResearch Other Characteristics relevant to the strength or weakness of a marketExamples:Landlord vs. tenant-friendly state?

Maybe that would be an ideal position to take if you want to grow with the property you use as your starting point.