I figured since I need to replace the roof, rafters, flooring and subfloor, I might as well raise it up and turn it into a 4 plex.

All buildings have leaky roofs, faulty heaters, poor foundations and very dated interiors. 

All buildings have leaky roofs, faulty heaters, poor foundations and very dated interiors.

All buildings have leaky roofs, faulty heaters, poor foundations and very dated interiors.

All buildings have leaky roofs, faulty heaters, poor foundations and very dated interiors.

All buildings have leaky roofs, faulty heaters, poor foundations and very dated interiors.

Also has the landlord pulled any permits for updates to roof a/c heat, utilities.

Made a claim for the roof and it was fine but then I had a renter commit suicide this year. 

currently HELOC rate is at 3.00%, down from 3.99% a month ago when the 6 month initial lock ended (i have over 9 years left on my draw period). now the rate is variable. the bank is hinting that the rate on the mortgage will be around 3.5% fixed. i don't qualify for traditional mortgage on my dti (but i do double my income with overtime and bonuses, and my wife will have a new income as well once we relocate) so our family friend is cosigning on the mortgage with me. the bank is writing it internally at 15yr with a choice between amortized or balloon. the building will need a new roof in about 5 years, and leaving $35k in the HELOC for that would keep me happy, so i'm willing to go up to $100k down payment if it makes sense. that would change my loan to $179k from $223,200, but also would tap any funds i might have for improving the property other than the roof, like fencing in the backyard and converting the third floor to its own unit. the new rubber roof would be more like $20-$25k but i like to be conservative. i have heard of people using their heloc to pay down their mortgage principal, which i could also do, but it seems to be a gimmick, and even if not may it be easier to just get a smaller loan amount to start?

You will own a property that has these risks and 100 more:car falls on leg of customer and he is young and incapacitated and sues you tootenant pours poisonous degreaser into public plumbing an it leaks 200 feet to neighbor properties, they sue yourobbery happens and child is trapped in the bay and survives, the parents sue youteen comes in with their helper dog who bites clients, they sue youfireman falls through the roof in a fire (chemical fire) and is disabled because the roof wasn't to code...Although you are only the landlord you have duties to health and safety of the employees, clients who walk in, and the community.Look up: Ng to the Ghost Ship landlord in East Oakland