I'm gonna tag @Elise Bickel Tauber in this post as she's definitely the right person for you to get in touch with in terms of investing in the Pittsburgh market - smart move by the way. 

Another thought/ long term plan I had was to make it a mini unique airbnb multifamily as in, have a silo home, then maybe put an airstream on it and lastly maybe an A-frame cabin.  

Have a legal advisor or counsel review your documents before signing.These will make your ultimate exit strategy, post Hard Money financing period, much easier when: - preparing & submitting paperwork for individual tax returns - maintaining the note in good stating with consistent payments & digital payment history paper trail - digital and/or easy access to documentation - preparing for a Re-Fi, Conventional financing, payoff, or even Flip/Sale & deed/title reconveyance to remove the Hard Money Lein holider at the end of the note's term

The nice thing about real estate investing is that there are SO many opportunities and strategies to help support your short and long term goals.

Second, in terms of asset protection, LLCs are not invincible, but I think what many don’t understand is that they are not designed to completely shield your assets from liabilities, on the contrary they are designed to contain and isolate liabilities.

I truly enjoy the diverse sets of experiences, learning from failures and successes online, and different ways to approach a decision.                                                                               

I would probably borrow a little more than $100-$150k if I could to keep more reserves.All I can do is mention my favorite fellow long-term operator and handyman in P-burgh @Jim K..

Share examples of pitches that led to successful funding and analyze what made them effective.Discuss mistakes or pitfalls that can turn potential lenders away and how to avoid them.

Many reasons here, but the most common is they went into deal with short term floating rate debt at a market peak.

One company I have seen success with being used is Waivo Insurance for STR.