I'm looking to refinance my existing investment property to purchase one in Pittsburgh for the purpose of short term rental am crazy to do it in the current market situation with Airbnb being what it is ? 

We currently only have one other townhouse that rent out.

You can also call your property manager if you use a professional management company to see if their portfolio has anyone that recently purchased or currently owns properties in the area that are thinking about selling (just to help you rationalize your value better).

Investing with a Friend: Do I need to set up LLC in my current state or the state in which I am making investment. 

I'm glad to see you're considering a multifamily home in Portland—it's a fantastic way to get started.Portland can indeed be a bit tricky for multifamily properties, particularly with the current market conditions and tenant-occupied units.

We are just… at our wits end currently …. and just want to be done with this stage in our lives, yet we are running blind here… Ryan

Current lender is Guild but sounds like they need the oven installed 

Or another work around is taking on a DSCR loan on your current investment property and using the cash out to buy another property. 

@Zachary EngenRecommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder, etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

It currently cash flows $300 a month on a $1200 a month rent.