He's out of the country right now for business and most of that responsibility landed on me so I'm managing a small business while thinking about how I can start investing with what I have. 

Pittsburgh, PA - considered to be one of the most rapidly gentrifying cities in the country, which improves prospects for appreciation.5.

I have no idea what part of the country you are talking about - also your profile page gives no clue about where you invest in.  

Especially with STRs- cities all over the country are reeling back on these and creating all kinds of rules for when, where and how you can have a STR.

Would this be in the form of cross collaterizing my current portfolio with a single lender?

It's happening throughout the country. 

Just be careful because getting a mortgage based on the idea this is a residence for you and then renting it out has legal implications that you don't really want to cross.

@Joseph HughesNew York tax law is one of the most complex in the country.

Especially since BP and Shell recently cancelled refining JVs with a certain Eurasian country that will not be named.

Let me know if you need a referral, I know some good ones all over the country.