Additionally, do you all generally use a smaller income criteria if the rent is inclusive of utilities? 

In trying to be more helpful, I came up with two additional ideas:1.

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.  

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

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!

With your additional $100,000, you’d have a nice cushion to renovate or furnish a property like that.It really comes down to how involved you want to be and your long-term goals.

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?

There had been a recent addition of, call it, Landlord LLC.

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. 

What happens if you lose on it, you now have an additional liability, not just a loss of money.Are you planning on keeping the current property or exchanging it (1031) into something else?