In the time since I first joined biggerpockets,  we've launched a roofing company that's being franchised nationally, a toxicology lab, a scrubs company with Patch Adams' foundation, and a handful of other ventures - but investing in real estate I feel like a permanent neophyte!

Just make sure your numbers work and your fiance is cool living with another family under the same roof.

Reshingle the roof - just asphalt tilesNew AC unitWe think there is mold in one bathroom and under kitchen sink, so some mold removal. 

And with the roof being 5 years old I feel good about limited capex in the near future. 

The unit is on the roof with no access except by ladder.

The roof has an unknown age as no new permitted roof has been pulled in the past 30 years, but no appearance of roof leaks currently, but looks aged.The bank asked me to give an offer...Comps in the area have sold in the past 12 months from 110-119k, rents seem to be around $1000-1100/month

Major renovations are planned: new roof, new HVAC, tearing down walls to increase HLA, licensed contractors on the premises, and some earthwork around the house to prevent rainwater drainage going through the house foundation.Thank you in advance!

Hey I'm sure you've found someone, but If not I have reputable contractor in Oklahoma that has been in the business for 20+ years in roofing & construction.

Undoubtedly there will be some repairs to be made with this many tenants under one roof. 

A contractor is proposing to do the roofing and siding through my insurance, he says it will save me out of pocket money.