@Dominick Marschall first of all sorry for your loss. 

No loan, all cash.The expenses have been divided by categories (materials, utilities, paid contractors, insurance, other outside services, etc) and listed on the 1120S using TurboTax Business.My question is, how do I determine the Total Assets for Item F of Form 1120S?

Should I obtain the HELOC now before a possible market correction (and possible loss in equity) for cost of $1000 or wait to see if I'll need that additional money at all for deal #2.If I buy a property for $200k to $400k that needs rehab, I'll probably need additional funds.

I think the biggest concern I have is that you are calculating your "cash flow" without factoring in ALL you expenses.Lets say you are "losing" $1000/month....but it would cost you $1200 to live somewhere else.... so you aren't really losing that full $1000/month....since you have tax benefits, equity, possible appreciation etc etc.......but do you have the cash to deal with that "loss" and be able to afford the expense that will come up..... the upkeep, repairs, rehabs, turnover etc etc.....other expenses WILL come up....not IF but WHEN....When you are accepting short term "loss", you are counting on a long term payoff, often via appreciation....plus you have to have deeper pockets to weather that loss for extended periods

For the finer details, I'd suggest reading a book or two and/or speaking with a good real estate agent, lawyer and CPA that understand investing and can help you with many items on your list.

There is an advantage that you may not have thought of, if there is a partial loss ACV coverage will pay out less. 

If I was determined to follow my expensive dream like this (maybe think of it in terms of wanting to buy an expensive luxury item like a boat or a car) then I would put off acquiring it until I have built a better base of income and savings.

To paraphrase this idea - your outsourced accounting partner should by performing the work and proactively providing solutions, as opposed to giving you items to research.

Here in VT, you only have 14 days to issue an itemized list.Good luck!

Also - One "Best Practice" item would be to make sure you notify your losing bidders, just a quick call to explain that you've selected a different contractor for this particular project, you appreciate their time for putting together a bid, and that you hope to work together in the future.