Since I’ll be doing both STR & MTR on the same condo, would regular long term rental insurance be fine along side with the VRBO/air BnB insurance that they offer ?

Those are my thoughts and the things you have to tighten up if you actually want to offer this as a service. 

I'm having to offer this as a fully furnished house to be able to charge a premium on rent just to get close to the mortgage.

Do they offer to help you collect or file a claim against them?

We still do not have enough inventory to meet demand which is why we still have multiple offer situations in most parts of the metro arear. 

What would you do in my shoes I don’t invest there so take this with a slight grain of salt but I’ve heard multiple stories of basically this exact scenario someone getting offered a big payday for something in Cumberland, rejecting it & always for some reason (house burned down, block got worse, sheetz decided they actually didn’t want someone’s land for a car wash after all) always selling for like 10-20k and regretting not selling. 

As I am exposed to the different products offered by lenders, I am trying to see how to best mesh hard/private money to be as efficient as possible.

Dealcheck is FREE and it offers an app for calculators.I’m shocked that that your team hasn’t told you how much your ROI would increase and user engagement just by having an app.

Explore Financing OptionsChicago offers excellent financing opportunities for house hackers.

Ask the seller if they can offer seller concessions to help cover your realtor fee.