That is my biggest obstacle as well.

Tried wholesaling  for a while to get the capital but seemed very counter intuitive since I was spending more money and time than I was making, just to gain traction and I was selling all of the good deals 🤷‍♂️That said, does anybody have any tips on how to overcome this obstacle? 

Because the property has 3 detached houses on one lot (a 2 bed/1 bath, a 1 bed/2 bath and a 1/1), I thought it would make a charming short term rental because guests can have an entire home at an affordable rate with nice shared grounds/outdoor space.

Welcome @Stephen Fahey I’m a sound mixer for TV and film (TexasSoundGuy.com) and the biggest obstacle you might have is the lack of a W-2.

Low fee, no desk, low overhead brokerages like eXp, HomeSmart, etc may provide less obstacles for agent-investors.

I have gone through quite a few trying to find the right ones to add onto and build out a detached garage as a small apartment and even getting those numbers to pencil out requires prudence. 

What kind of obstacles would I face in trying to do this?

Rents were far under market, zoned r4, detached garage is getting converted to ADU eventually, etc....Currently looking at the next property and will be able to rent out the side I'm living it.

I have tried several banks to do a cash out refi and am running into obstacles as my properties are in LLCs and the banks are looking for a full income to debt ratio check on me personally. 

What are the obstacles that you think a 1:1 coach would help you overcome?