Theirs lots of money out there and there figured out this vertical is a solid place to put it .We just noticed a company that took a commercial property public in NY.They specialize in crowd sourcing funds and place theme is our space with realizable returns Ahhh change .It will all be about keeping up and educating our investors on how they can/should compete as we see more and more of this .

Conforming loans backed by Fannie/Freddie are only made to individuals and not business's so anything outside of this would be a commercial or private loan.

I am looking to buy and house hack my first home (STR/rent individual rooms in the house).

The competency of the property manager is far greater than whether he/she lives on site.

In addition to that, I don't even think you can own an STR in an LLC as permits are only issued to individual owners. 

You can also have individual subs do their own drawings. 

It is probably very individual what will trigger you to take action, but motivation, consistent learning and perseverance will eventually bring you where you want to be.

I understand that individual circumstances play a huge role, but am curious as to what you would recommend based on your experiences. 

There is ALWAYS something to learn from every individual on this planet.

It's a bit pricier than most options if you hire it out, but it's actually a pretty easy DIY job if you can do it yourself or have an hourly person you can hire to do it competently.