So the furnace and water tanks have been compromised; they estimate $6-7k for replacement. 

Am I playing with fire in regards to the properties being part of a business and compromising my umbrella insurance coverage?

Women only teams are great but restricting ourselves to that might compromise our opportunities to learn.Their M1 group is for non-accredited investors whereas the regular one is for accredited investors.

My thought is since the windows are already compromised they could easily deteriorate further with normal use and then it becomes a capital expenditure.  

The whole problem with LLCs, rentals, and corporate veils is that the LLC rules are practically nonexistent, when that is the case, lawyers figure out what you can/can't do based on case law, but there isn't enough case law out there to let them know *exactly* when the "corporate veil" is compromised.

The problem has existed long enough that there is a decent chance ceiling joist & exterior framing have been compromised

We don't have the cold temps that you might experience up North so maybe that is cause for concern.Have a plumber perform a pressure test on the house and that will tell you if the plumbing has been compromised.

It is much easier to make those choices before you have children or other responsibilities, but it also may not be worth the hardship if you can have most of what you want but just need to put up with some weather and compromise by planning some tropical vacations or something.  

I understand that the condition of the property itself may result in compromised collateral for the loan, but for cryin' out loud, that's why hard money lenders charge 5-8 points going in, 10-15% interest and a one year balloon.

You compromise.