We are having a hard time coming to a consensus of how to identify, underwrite, and basically take the jump. ( we don't want to screw it up lol) I've searched this topic on the forums but figured someone could give some insights given our situation.

Situations like this highlight how important it is to work with reputable lenders and do thorough due diligence. 

As soon as interest rates or your personal situation are favorable you can then refinance at any time and eliminate the hard money lender.

That being said, we have an incomplete picture of your personal situation so please take this advice with a grain of salt.Good luck with your investing journey!

If I uncomplicated the situation a little, do you have any advice on how we could make something like that work?

We are working to help people evaluate their situation and manage properties while these court actions are in process.

I really feel this financing situation is holding me back from going and finding a deal.

I specialize in 1031 exchange, investments, and creative rental strategy so I can confidently and deeply analyze your situation.

You will certainly gets lots of different perspectives from the forums and most likely multiple people will have experienced a similar situation in their investing journey!

The situation is regarding a mutual agreement both the landlord and myself made regarding the painting of two rooms within the property we are renting to a neutral color (rooms are currently purple and lime green).