You've asked a lot of questions, and you should, but I want to help you focus on a concept if you want to scale.

We scaled down the short term rentals simply because while not hard, that model seems to be more of a distraction now.

If you are planning to self manage you won't need Guesty until you scale. 

A good HOA leverages their scale to get solid and reliable vendors.

@Travis Houck i'm going to be the first to tell you that you should probably abandon that idea until you get some capital and experience. unless you can find a partner who has what you dont, i recommend scaling that idea back a little bit.

Preferable 4 Plex first, then scale up.

You can have a written agreement that any deal brought directly to them is grounds for your set and agreed fee (or perhaps a sliding scale fee if you wish), or you can prearrange to set up a legal entity in which you name your buyer as part owner, make your offer to the seller in that entity and then sell your shares of the entity to your buyer/partner for you fee.

The property management company is small (Approximately 50 units under management), but is well positioned to scale.

When buying a single house, you are likely not receiving any type of discounts in regards to property management, materials, leasing etc.Take the same $50,000 to invest into a passive deal, even though you may only own a fraction of the asset, you are achieving the scale of having many other investors invest along side you.

We usually upgrade to heavy duty pro-grade LED lights - it is in our best interest as a property owner because it prevents future issues and makes the residents feel save, so they stay longer.