The lower unit owner has contacted her insurance company as well as Serv Pro to assess the damage.I called my insurance company and they said that my insurance would cover my unit, while the lower unit owner’s insurance would cover her damage.With the above in mind, I’d imagine her insurance company would look for someone to collect the money from.

You must have monthly utilities, and taxes/insurance to pay, supplies to buy, monthly fee to the building, etc, so your net earnings for August must be less than $1114 if that is what you got paid out.

@Nick if you are self-employed and couldn't make your payments (not just on your real-estate, but on other debt and bills) for a few years without your income, I'd get short-term and long-term disability insurance in place for you and any other breadwinner if you don't have them, they are expensive, but will protect your assets and lifestyle for your family in the event that something happens, regardless of a downturn.

A Quit Claim Deed invalidates a lot of Title Insurance policies.

Typically lender will require property to debt service 1.2/1 - meaning if the mortgage payment including taxes and insurance is $1,000, monthly rents must be at least $1200.

I believe I have 2.5 options:A) Keep adding to this fund over the next few years until it reaches $300k+ and qualify for a $1mil+ loanB) Use $100k to buy a $500k single family home and use as future leverage for option A (Deposits <20% of property value incur an insurance fee of 1.75% called LMI) C) Use a 5% deposit/$25k for a $500k property, cop the LMI of $8500 but get in the market most soon and then leverage for option AWhich would you choose and why?

If not, you would likely need to account for that in your expenses. 2) I would make sure to factor in lawn care / snow removal (if applicable)3) Lastly, I would make sure to add insurance into your expenses.Otherwise, your numbers look good (although I cannot attest to your rent estimate as I do not know the area). 

Do you see any issues with insurance companies not wanting to insure it unless all wiring, plumbing, among other things, etc. is replaced?

While inconvenient, the fence could have a latch that can only be opens from the inside.A pool alarm, a floating device that detects waves, is also a good idea.Obviously, your rental insurance has to be made aware of the pool....they may have their own requirements.

There’s other contingencies you can use too, financing, feasibility, environmental, neighborhood review...Have your DD start the 1st business day after they provide you with all the documents, P&L sure, but also you’d want title docs, details on mechanicals like age, repair history and warranty status, insurance claim history for the last 5 years, every scrap of detail on any pending claims, zoning use confirmation from relevant govt entity, copies of all docs they have received from any govt authority related to the property for the past 5 years... there you’d be looking for code violations, notices from EPA or fire marshal, etc.