In the end it will all work out.

I recall reading about it in CNBC...The quest for solid returns in our current market might feel daunting with interest rates where they are, but the good news is.. if you find the right deal and set clear criteria.. like a minimum cash flow target, or a plan for eventual refinancing.. your numbers can still work out.

That's 130% interest when you work out your ACTUAL cost.

I go in with an intention and optimism but once you're in it things work out the way they do and getting your calculator out isn't going to change that.

Plus, if one area doesn’t work out, it’s probably much easier to sell a single-family home than an entire multifamily propertyBut again im not an expert, im actually hoping for some guidance here as well

There are also deals that can be find on jud.ct.gov for foreclosure auctions but those rarely work out because the people usually owe more than the property is worth or they get cancelled and postponed frequently. 

Plus I'm in a very HCOL so the math for short term rentals would not work out.  

These old houses built 70-90 years ago seem to never break once I work out all the kinks.

If so, how is that going to work out among the other tenants? 

Quote from @Rhyse Andrews: @Erin Helle1) try to squeeze in some tutoring sessions for mid terms/finals before schools go on break.2) set up EIN and a business bank account  Love it. #2 won't take long at all (less than 2 hours total) and will set you up nicely for next year!