I work full-time as a CPA audit manager at a Big 4 public accounting firm, and in my free time I would love to help and learn from an experienced investor with strategies similar to what I’m interested in (appreciation, single family (potential multi family), mid-term rental (potential short-term)).Open to any advice as well on how to make my first leap into actual investing!

All of those are "part of doing business". 3 years, 7 Airbnbs and hundreds of guests later I'm still a proud host and a big fan of the mid-term / short-term model!

Those costs factor into the investment and I think technology is going to go a long way in reducing the costs for vendors, lowering the costs for buyers and helping Roofstock bring about a better experience for the investor.  

They also don't factor in how long properties are sitting vacant at that price and also don't factor in how long tenants stay at that price.

How do you estimate just how many residents will stay long term vs. decide to leave or perhaps pass away during their stay?

In this case, rates don't matter as much as lower closing costs, since it would be short-term.  

Need a new roof in a 3-5 years, you probably want to be pretty liquid (year long CD, Money Market, maybe very short term bond fund etc) for those funds.On a condo board 15 years ago, I  was once able to get us into some nice CD's a decade ago that laddered with the useful life of components.

Best bet is to contact your trusted lender or other financial institutions to compare offers to find the best interest rates and terms that suit your investment strategy.  

The house currently rents for $1450/month, we have long-term tenants, and we use a management company.

If you're looking to invest long term and build a portfolio, I'd recommend going with a 2-4 unit and take advantage of the VA financing.