@William Jasin:I think you received bad advice on multiple grounds.

He also does keeps the grounds and does the repairs.

Just in the exploratory phase now.  

You need boots on the ground to win here as the structural issues are really significant.

There is also an unfinished large attic area.I have an option to dig down the ground and bring basement ceiling height to 7'6" and duplex down from 1st floor for large unit 1 and then duplex up for a large unit 2.I have another option to try changing zoning from current RS3 to may be RT-4 or something so I can make the basement as legal after I dig the ground so building can be legal 3 unit.The building is surrounded by B1-2 zoned building and it seems weird that only this building is RS-3.

Have trusted boots on ground there. 

Size:  Above Ground 1,660 sq ft/ Unfinished Basement 350 sq ftI'm looking to update below items:Exterior: New roof and window (as needed)Yard: Cut big 2-3 trees in the backyard, clean front yardInteriorBasement needs mold remediationNew kitchen (cabinet, appliances, & etc)New Bathroom (2.5)Move/remove walls Add ceiling wallAdd insulationelectrical work (if needed)plumbing (as needed)new paintNew floorIt pretty mush needs a complete renovation.

Size: Above Ground 1,660 sq ft/ Unfinished Basement 350 sq ftI'm looking to update below items: Exterior: New roof and window (as needed)Yard: Cut big 2-3 trees in the backyard, clean front yardInterior Basement needs mold remediationNew kitchen (cabinet, appliances, & etc)New Bathroom (2.5)Move/remove walls Add ceiling wallAdd insulationelectrical work (if needed)plumbing (as needed)new paintNew floorIt pretty mush needs a complete renovation.

I would like to get into investing with a few family members, but I want to see if anyone had ground rules, that worked well for their group, that they'd be willing to share.Thanks!

He issued a construction loan and built 2 from ground up then switched loan to variable.