Basically 1099s are used to report when you aren't paying payroll tax, but are "employing" someone.Hope that helps.

., one big issue is that using your model of "flipping" you will not be able to use the 1031 exchange so you need to put ordinary income tax + Self employment etc into your proformas to make sure you can still get the return you want.1031 exchanges are for property that has been held for "productive use in business trade or investment".  

I don't have a property in mind, but I would like to know if I could even qualify before doing the hard work of finding something and then getting a big denial.I've served and worked in restaurants for 3 years and same goes for my boyfriend (A little over 1 year at our current employer).

Since it was becoming winter and we needed to keep our workers employed, I told him that we needed a minimum of $10k profit.

It may seem selfish, but retirement is a longer term horizon and I can help the kids find a combination of methods to go to school.  

Although in many cases corporations will simply buy the properties and become the landlord as well as employer.

I suppose the pros have their reasons as they wanna make their money, & profit off of any method they can use. 

It can take less than 48 hours to verify a tenant's application if I can reach their employer and current/past landlords.I can wait that long; if the tenant can't, that's a big, red flag to me.

Tell Lars that Chris Mason sent you.http://larsghanssoncpa.com/ When his office and mine get conspiratorial with the goal of boosing purchasing power of a self employed person a tax filing or two out because someone's purchasing power is artificially constrained by stupid mortgage guidelines, amazing things happen.

Strategy should encompass what areas you're targeting, how you're going to market to those areas, what methods you're going to use to purchase property, how you will monetize those purchases, and what your exit conditions are.