We also require that we be added to the contractor's insurance as Additionally Insured, so we're covered if they cause damage or liability issue.3) If the property is occupied:- One of our people MUST accompany their person (and we charge for this). --- We were sued many years ago, along with the owner, because tenant claimed owner's contractor sexually assaulted them!

My goal is to live in the home during the winters, maybe 3-4 additional weeks for vacation, then rent it out to help cover the mortgage the rest of the year.  

Cash-flow is for "keeping the lights on" as in covering operational expenses to defend against any need for additional capital investment. 

What do you mean you are paying $400 additional dollars more than what you are paying now?

Both properties have a substantial amount of equity that’s essentially sitting idle.Would it be a good idea to tap into this equity (through a HELOC, cash-out refinance, etc.) to fund future fix-and-flip projects or purchase additional rental properties?

Of course they would want additional appreciation on top of principal but any DST sponsor will tell you that they factor in the up-front load on their underwriting and  likely will overcome that up front load.

I play it with my kids every once in a while. 

Exactly 1 year later my first tenant moved his family in where his kids and dog can play in the massive yard while raising 2 cows in the barn.

Well no kidding!

Suggest you check in with him/her on this additional service as your attorney is already intimately familiar with the file and you can often give them pre-authorized amounts to settle on vs trying to squeeze all the blood from that turnip.