When you own a couple of units, the odds of there being unexpected vacancies that overlap each other are usually low, but when you acquire more and more real estate, the odds of tenants moving out around similar times increases. 

I am new to real estate investing and looking to connect with any local (DMV) investor.

Even if a software is free or cheap, it's the time investment getting things set up and then tweaking it for the first few months that is the real "spend".

This is a new venture that I'm looking into and real excited about. 

If a wholesaler can still profit while provided “full disclosure” and adhering to the rules and regulations of real estate licensees then they’ve earned their profit.   

@Destiney E Goins - Welcome to BP and real estate investing, Destiney!

I honestly don't have any real feedback on them yet so hesitant to "recommend" them. 

Also, if your wife and her parents were the real estate investors first, why aren't they weighing in? 

Anyone that is looking at your assets is always going to need to factor in property management, so you can show that as a real expense (and really make it as high or low as you want).I work in a vertically integrated real estate and development company, and I cannot imagine how things would run if we did not have an internal property management company that essentially works for the other companies but also stands on its own.

I would like to speak with local investors, real estate agents, property managers, lenders, etc. from the area.