Need to replace roof within first year of owning rental

[Andrew Sucato]

Hi everyone! I purchased my first duplex last May and am house hacking it.  I have learned a ton over the past year, and have been bitten by a few maintenance issues that have cost some big $$.  Since I am only a year into the property, I have just under 1000$ in the maintenance fund.

Currently, I have a leak in a 20+ yr old roof (not a direct result of hail or super extreme winds) over my tenants side, and going up on the roof, there is a lot of decking that is spongy and seems like it has been letting water in for some time.  I had a few roofers out to see if we could repair, but they all said it really needs to be replaced since there is are a few boards that are really spongy (and I agree with them).  To tear off and replace, I am looking at 15k before replacement decking (had a few quotes from both established crews and side-job roofers).

I also had a leak a few months ago after a hail storm that I tried to go through insurance, but the claim got denied because there was not enough damage to break my deductible.  So I don't know if I should try going through insurance again to see if they will replace, but I'm a worried I'd get denied again and they would shoot my premium up.

From this I've already learned that I need to do more due diligence up front so I don't get hit with a roof replacement or other similar expenses less than a year in before a fund is established (or work a deal with the seller to offset that expense).

So, I wanted to get opinions of more experienced investors as to what they would do in this situation.  Would you try and go through insurance again? Would you try and get financing since the maintenance fund can't cover it? Or would you just eat the cost out of pocket? Or something else?  Luckily my personal finances are in order where if I have to eat a 15-20k roof out of my own pocket that won't drown me, but will set me back on my goals of scaling.

Thanks in advance for the advice!

[John Clark]

Quote from @Andrew Sucato:

if I have to eat a 15-20k roof out of my own pocket that won't drown me, but will set me back on my goals of scaling.

Thanks in advance for the advice!

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You're a rookie. You might not even like being a landlord when all is said and done. Scaling up when you don't know if you even like being a landlord is the last thing you should do.

Personally, I'd pay out of pocket and get the roof and decking done and done right. The pain of the hit is what you'll remember, and you will do home inspections and due diligence more carefully net time. It will also slow you down -- for your own good -- and you can see how you like being a landlord.

It is important to start. It is not important to get big fast.