I'm trying to get better at gauging why certain properties have not been touched by buyers, and sit on the market for 9+ months.I found a multi-family listed currently listed for $57,000, that has been on the market for the last 9 months, and reduced its price by ~2% every 3-4 months.It consists of 4 units rented with $1350 total income.

.$52k in total going into this deal.LLC will be owned in unit = $1.You own 21%, Wife 21% and Partner 58%.

I totally agree 65th Center is okay area.If I recall correctly 65th Center is surround by a lot of small businesses.( stores, activities, beauty and barber shops, etc )Most family that would move into this apartment building would be looking for Wauwatosa education for their children.Just my two cents

If I bought two places each for 300k, one with 5% (15k) down and one with 20% (60k) down, I could rent both out for a total of $3600/month, and a mortgage payment of $2500/month.

If it will work with the 50% rule (or less if most of the utilities are separate and you plan on self managing) and a 30yr fixed @4.5% for $285K and assuming you live in the 1BR you would have $1,700 in expenses (I never reduce those just because you live in a unit, just my opinion) and $1,444 debt payment for a total of $3,144.

Herb Bleacher of Black Knight Financial (Formerly LPS) said; “While first mortgages are almost half the levels as one year ago, total home equity loans have increased by 70%”.

Insurance is cheap ----------and totally unnecessary until the tenant burns the house down with a space heater, or a tree falls onto the house or lightning strikes. 

While it totally depends on your market, many markets have a definite "moving season".

Very different if the buyers were bringing their own financing from a bank or other lender but this just seems totally unrealistic.

Totally makes sense from a cash flow perspective what you're doing.