I just completed the inspection yesterday and it seems the roof will need to be fixed(over 20 years, the boiler system is very old(there are 3 boilers), one of the 3 hot water heaters(HWH) is leaking and the 3 car garage (which is one of the main reasons the property is compelling as an investment purchase) is not structurally sound and may need to be demolished.

I just completed the inspection yesterday and it seems the roof will need to be fixed(over 20 years, the boiler system is very old(there are 3 boilers), one of the 3 hot water heaters(HWH) is leaking and the 3 car garage (which is one of the main reasons the property is compelling as an investment purchase) is not structurally sound and may need to be demolished.

Roof and plumbing appear to be OK.

It's got some deferred maintenance so our contractor is slated to start work this coming week, new roof, bath remodel, windows etc.Now I'm wondering if we should be adding a third bedroom instead of just cleaning it up.

I would check the big items (Water heater, HVAC system, roof, windows, appliances, etc.)

The renovation cannot be for any structural changes, i.e. you can't change the floorplan to have an open concept between the kitchen/family room or add an additional half-bath, but you could redo the kitchen, roof, etc. 

I did actually go over budget by $15000 between unforseenn wood damage and roof replacement. 

Do you find it difficult managing multiple people under one roof in the lower income classes?

@Frankie Woods  I'm mainly interested in multi-family as my tenants would be under one roof and I feel that I'd be able to pay the property off quicker due to multiple rents. 

Roof, HVAC, foundation are the big 3.