Larger apartments are more of a fee play vs cashflow but offer greater appreciation through value add on the exit. 

They are keeping all the slots full year round with very little maintenance.

This would solve your lack of immediate funds to float this deal AND will offer you a much more valuable property with a NNN single tenant lease in play. 

Do they always run a title search or do they just play the odds?

It seems that there are some silent cap rate factors at play here that people are forgetting .

The advantage is you are all on a level playing field.

Obviously building conditions comes into play but you need to look at the operating expenses & the current rents coming in.

This is where a trusted team comes into play  Plenty of better investments in Milwaukee to be had if you look.

Family has stated they would not mind renovations and would prefer for it to stay in the family although I am slightly nervous on how this would actually play out as my grandparents built this house in the 60's and we have tons of great memories there.

If you are a street performer playing a saxophone and someone walks by without giving you money, do you keep playing and wait for the next passerby or do you chase after that person like a lunatic and say "don't like saxophone?