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I co-own a STR PM Co with around 90 doors currently and am also a broker who specializes in STR Investor acquisitions. 

@Jordyn Ohs pay off/down your Heloc aggressively and/or look into DSCR loans for future acquisitions.

The underwriting process is certainly more arduous than most acquisitions but through my personal experiences some of the lenders are far more knowledgeable about the requirements and make for a far easier process for both seller and buyer.

And what a great acquisition price in Fair Oaks! 

For over a decade, I’ve focused on multifamily acquisitions and asset management with firms ranging from small boutique offices to large syndicators.

Unresponsive customer service leads to not reaching out to Obie again in the future for other rental acquisitions.

Why do their deals need capital infused, and are those reasons due to poor management or things that were truly out of their control and/or could not have been foreseen at acquisition?

It seems most off market deals I've found have been from larger acquisition groups.  

HUD 223(f)'s take a long time to close (6-9 months, sometimes long), so they are not a product that you want to use to facilitate an acquisition (only use HUD 223f loans to refinance properties that you already own).