He's looking to finance MOST of the deal through conventional financing, but may need some extra cash options for a small amount. 

Unsure why is would increase to this amount either. 

I would have enough money at that time to pay that amount.

Pick a fixed amount of time, ie: 3 months and set specific goals. 

From the sounds of it, I’m leaning on assigning a weight restriction, and limiting the amount of dogs and breeds a tenant can have on my property.

Minimizing the amount he walks away with( its a cheap deal to begin with)Im confused about the title insurance/judgment clearing process.

The cost of the tree guy is 100% your cost to bear, regardless of amount. 

If not for BP, I would have never thought to use the BRRRR strategy and House Hacking on this property and would have just thought of it as a lost cause because of the amount of work needed for the unit.

I would go with syndications with that amount of money & study & look at many to become an expert & build a portfolio.

We are doing a 1031 exchange however we are having issues getting pre-qualified for a mortgage for a rental property that would equal the sell amount of the original property ($425k) due to changes in jobs and relocating etc.