Hopefully we will be functioning at 100% in the next week or two. 

Also, in your response, let me know if you have used only the one you recommend or if you have used multiple, or even if you have a friend/colleague who uses a different software and has given you a review on that particular software.Pricing is always important, but functionality/usability is more important.I am trying to get up and running by June 2020.

After all, you want people to imagine the house as their future home.Again, this is stuff agents deal with every day since their primary function is to sell houses - and I mean sell in the salesperson sense (not coincidentally, agents who aren't brokers are all "salespersons").

I'm frankly surprised that your attorney suggested combining them.

If you put together good systems you can avoid that somewhat, but I can say that I deal with more problems on my one property in a C class neighborhood than I do on all of my other properties (which are in B class areas) combined. 

I see where you're going with YM vs SD... one way is Data Validation list with YM or SD, then into a nested if/then function, but within the nested function, you may need a max of say two criteria from your lender for YM. 

I have an investment now where my net cash flow is more than my Mortgage (PITI), water, and utilities combined.

My first and HELOC combined are $510000 and I wanted to pull out $100K to invest in another investment property. 

Sell it now, net gain about $40-$60K after taxes, commissions, listing price, etcTo properly and adequately answer this question, one would need to know your strategy and goals.Strategy A is based on cash flow to support living expenses.Strategy B is long term wealth building - appreciation (market and forced) combined with principle pay down, depreciation, etc.If you strategy is A, then you should sell as this will not turn out positive for several years down the road (unless you utilize some sort of house hack play, vacation rental to increase income, or any combo of increasing income and reducing operating expenses - which by the way you skipped a lot of those in your analysis so your negative monthly cash flow is actually greater than you explained.)If your strategy is B, then by all means keep it and enjoy the likely future appreciation, amortization and depreciation deductions to offset your actual loss each month until the unit goes cash flow positive.

Combine that with losing the value of compounding, usually makes 401k/IRA loans a losing proposition.