There are a few different ways to go about either 1. getting the existing tenants out a little more constructively  (and much less risky/problematic for you) prior to closing or 2. finding properties that have already been vacated.Feel free to send me a PM (private message) if you have any other questions or would like to discuss this further.

Key components of property management (leasing and renting) are considered real estate activities under existing Wisconsin real estate licensing laws.

I plan to use my schooling, degree in finance & Economics, to closely analyze deals hopefully keeping my portfolio's risk-reward ratio as beneficial as possible.

Not being greedy and will to wait for delayed gratification rewarded you very nicely.

But if your position is such that you can find cash from other sources including tapping the equity on the existing condo in a 2nd or refi or savings for a short term or whatever, you can go that route as well.  

As far as seeing rental income, if you own the house cash and don't depend on the rental income as part of your application income, it really won't matter if you show it or not, and there are different rules when they will consider it income; my bank goes from your tax return, so if you don't demonstrate rental income on your federal 1040 it doesn't exist. 

Sounds like you are well on your way and will be pulling the trigger soon, I think at this point you should have been able to conduct enough studies to determine the major challenges that exist as you define multi and single family.

Multifamily housing is almost non-existant in Northern Virginia.

if you do a Google search "Brian Gibbons lease to own presentation" you'll find out how I talk to home Sellers, showing them all their options,  persuading them to look at the subject to existing financing, lease options, or wraparound mortgages

1) Josh has some media background in his past and seems to still have some connections.2) They're positioned their podcast format in a far more educational format so they have a very good idea on how to frame their content to deliver real value.3) They have access to one of the largest pools of investors and models of anybody else on the planet.Its interesting that so many investors on here complain about the existing shows.