I currently run a successful Airbnb and want to expand but am having trouble connecting with owners or real estate agents to help. Willing to pay finders fee.

When this thing turns around like it always does, you will be happy that you at least acquired the property. 

I acquired a 4b sfh through an online auction about a year ago and completely gutted the home and upgraded mostly everything.

In the last 6 months i've acquired two more short term rentals in the Poipu Beach area and completed a 1031 exchange.

I acquired my first investment property a few months ago and renovated the units as well as rented them out and its cash flowing well. 

Begrudgingly, we acquired the property.

Based just on your DSCR calculations, it appears this property is significantly under-performing, or if it is operating well, then it is significantly over-priced.If your plan is to reposition the property, then you need a bridge loan or private loan to acquire and manage the property. 

But if you are doing seller financing on assets you acquired in the last few years and did a cost segregation study, it is something to be cognizant of.There is also "1250 recapture" which is taxed as Ordinary income as well, and is not subject to installment reporting - this is when you took accelerated depreciation (bonus) on any real property assets. 

Here's my situation: My family has about $250-$300K that we recently acquired through a relative unfortunately passing away.

With youth on your side, you have ample time to acquire experience and expand your network.