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.  

This is our “retirement” money...insurance if you will in case real estate investing doesn’t work out for us.

Same with health insurance.

But, from my understanding, if something goes wrong that he should have caught, his insurance will cover the repairs. 

Does anyone have any suggestions for  insurance companies?  

It's in a nice safe area that I would be thrilled to live in.Now I'll go over some of the financials.Price of the property: $120,000FHA loan payment: $1000 (Rough estimate including loan, insurance, PMI, property taxes)Current rent per unit: $550, 550, 600, 600.