Alot of contractors I see in my area have a tough time getting ahead simply because their not good at managing the business aspect of the business. 

If you’re going for cashflow, that’s pretty tough to beat but if you’re trying to buy a house a year for 15 years and put them on a 15-year fixed am schedule and have a paid off house every year after 15 for retirement purposes, then it would be a no-go (for example).Also, depends on the work you want to do.  

Sometimes Holdco is used to establish a retirement plan if you are not ready to provide retirement benefits for employees.

In order to accurately analyze a property you will need to know the size and number of beds and baths as well as what all needs to be done which is tough without being inside the house.

That being said if one of us loose our job or get into any unexpected expenses it is nice to know we have the cashflow to fall back on if things get tough. 

The real estate community is a great place to start.For number two, it is tough, but do what you can to learn a market. 

Now, most of these smaller banks may only have 12 employees or so.

It depends on their preference and discretion as an independent contractor.... unless they're an employee of brokerage.

Now looking back, I kind of want to get a few STRs near Medical Center (yes I know that’s gonna be tough) and theme them out.

:P I know it's a tough market, but I believe that where there is a will, there is a way.