Buy cheap, be smart and work fast.

How does this roof shed water? I think that’s the first thing you need to address because it looks like water damage has happened.

Yes there's been water damage. The roof has a big hole and other smaller leaks in a couple of places. I need a roofer for that? Maybe that's the place to start?

Making something water tight, is always the first thing that needs to be done, so yes, a roofer is probably a good place to start. There is no point in repairing anything until the building is water tight. It could be a cute little building, once its repaired and clean.

Thanks @cat_ky. My tenant has been putting his cardboard boxes and other stuff all over the house, and it's beginning to attract bugs, roaches. Meanwhile, I contacted roofers to get quotes but we've had a few storms and they're busy. Long story short, this project could take a few days to get started.

If I put a big tarp over the roof so rain water doesn't get in, clean the garage, and have a pre-hung door installed, it may be good enough to have the tenant move his extra stuff here? What is the risk? The roof and roll up door can be worked on right after. Thoughts? If it's a bad idea, it'll be great to know now instead of mid-way.

Thanks in advance!

I dont see how the roof deck will still be any good if joists are rotted. You dont show any of the interior, but I would plan on removing the entire roof, including structure, reframing and installing a new EPDM roof. Alternatively, you could put a sloped roof with shingles on in for less money. BTW, You need to remove that tree on the high side. The roots will stress the masonry wall.

@Seabornman out of the 12 or so joists, 2 need replacement and 2 need to be reinforced. The ones that needing replacement are where there is a big hole. Doubt the whole roof needs to be removed (layman opinion) but open to your thoughts.

I would not count on any tarp keeping garage dry. I had major storm damage in 2020 and had to have a complete new roof. The old one was tarped for a week, and blew off with strong winds, 3 times, and had to be put on. Only one of those times, did we get rain with the wind, and it came in and damaged 2 interior lighting fixtures, so they had to be replaced too. I would not put anything in that building until it is repaired and safe to go in and out of, and has a new roof. Safety and water intrusion, are two huge factors in that building. I wouldnt allow the cardboard boxes there either, if they are drawing bugs and cockroaches. All sounds more like a tennant, that doesnt clean things up very well. Clean cardboard boxes, should not attract bugs and roaches.

You got that right.. this tenant is not particularly clean!

A tenant that causes a roach problem doesn't clean adequately. Fixing the garage won't fix that. It's unlikely that he'll move all the clutter to the garage, start vacuuming and live clutter-free from now on. It's probably worth fixing the garage, but don't expect it to solve your tenant problem.

This isn't a beginning level DIY project.

This is the type project where houzzers really shine. Go for it , you can rely on advice for next step along the way.

"This is the type project where houzzers really shine. Go for it , you can rely on advice for next step along the way."

klem1:

Right after I read that, my sarcasm detector spiked. Does it need recalibration please?

Rest easy Joe, there's nothing wrong with your meter. I just figured that's what cooly wants to hear. If he doesn't know by looking, I can't think of one thing I could enlighten him of. Flat roofs are one of if not the most challenging things to repair on a building and doors aren't far behind. I seriously doubt there's many amongst us that can do both, much less tell others how.

Knock it down and start over. With someone who knows what they are doing. You do not.

Knock it down and buy a shed to assemble on a concrete pad. That'll be the cheapest solution.

I see a little siding peeking in the picture, so I guess that one bay was enclosed to a living space. So this is where the tenant lives? If so, the pests are attracted to moisture, not storage. And being built into the soil provides lots of reasons for pests to be there. The trees/brush are exacerbating not only the pests, but the brick/mortar deteriorating underground, and should be removed. And water is coming underground down the hill and resting against the brick, so moisture is high inside the garage and converted unit.

Repairs done cheaply just to get by are indicative of a certain type of landlord. I would instead consider this garage an asset to the property, and think long term. You can easily close off the fascia, remount the door, and scab the roof leak over a day or two. But it may be good to come up with a real plan.