I would consider the type of property you are investing in or what type of tenant you are approving to see why you need to use intimidation to collect rent in the first place???  

It must be pretty easy to get approved for an ESA.

We have been approved for a $400k heloc since we have equity in our primary.

Hey BP I live in CT, with wells fargo all of a sudden closing my personal LOC, Now I can't even get a HELOC on my primary or any of my rentals and I have a nice amount of equity in there.. my DTI is too high. I fir...

But the procedures will tell you how they should present the extra to you for approval. 

For example, the upstairs units in my complex cannot have hard wood floors or tile in the bedrooms, they can only have carpet... and all renovations must be pre-approved by the HOA before they are completed.

I got pre approved for up to 400k and I’m wondering if in the crazy market I really even stand a chance to find something less than that?

I bet they have a list of approved education/licensing criteria service companies you can choose from. 

My handyman has been hard to work with on this and when I told him not to proceed until I could consider the costs, he said he already submitted a permit request and if it is approved I will need to pay him the $1,500.

You can do it as a joint venture where you partner will also likely sign and guarantee on the debt, or you can have an investor provide you debt.