I'm thinking plumbing, roof leak, and electrical? 

Victor,Before you start calling around I would recommend gathering some info:1. is there knob & tube or aluminum wiring2. when were the systems updated and was it full or partial updates: - Roof - Electrical - Plumbuing - Heating For the Electric a) are there circuit breakers or fuses b) what amp service For Plumbing a) any pex piping.

Some can tell you what color you can paint your house and what materials you can use on your roof. 

The house is in rough shape so we'll be doing a good bit of work:  new roof, windows, flooring, cabinets etc. 

Covet your thoughts. https://www.zillow.com/homedet...Purchase 105kDownpayment 25%Interest rate 4.2%Initial repairs/updates 5kWill need new AC and roof within 5 yrsRent 1100-1200 (sought after school district)

I can record expenses to the building (customer) for things like roofs, real estate taxes, insurance, etc, repairs directly to a unit, and record rent to a specific tenant.My properties are in an LLC, granted all the same, and it is a sole member LLC, so for bookkeeping, it all flows into my personal taxes anyways. 

You're going to need money to invest in it.

I’ll be getting inspections, and need more info on the plumbing and electrical as well as the roof before moving forward. 

@Larry Turner Rent Roll, P and L, utility bills, leases, property management, inspection, crime in the area, taxes, tax paid receipts, capital expenditures in last 2 years (appliances, roof, etc...).

Possibly Roof (due to recent hurricane in the area in 2018)2.