Thanks everyone for the feedback! @Jonathan R McLaughlin I've contacted lenders about doing a cash-out-refi. When I purchased the place 20 months ago the rates were higher and I was locked in at 5.4% I should be able to get a rate a couple of percentages lower so it really won't affect the monthly payments much. The neighborhood has appreciated (thank you free-market medical weed?) so I have plenty of wriggle room to take out the cash I think I need to do the roof.
@Daniel Smyth thank you for the info on dealing with the mold! I had a mold inspection done when my tenant first mentioned her allergies. The spore density was lower than the air outside, but a month later when I came out I could see pink stuff forming on a few walls in the utility room. On the report it said it was not a mycotoxin. I sprayed them with bleach and then with Kilz. I also applied the Gaco product on the seams of the weird flat part of the roof above, but that was in October so I have no idea what the walls are looking like now. The kitchen had an even lower spore count, and from talking with a remediation professional he said it was extremely low for a report, but it was a mycotoxin. He identified some mold behind the dishwasher by flashing a light under it and I was advised not to move the dishwasher and to rent a HEPA vacuum if I decide to do the remediation myself. The wall the dishwasher sits against is the exterior wall of the original house where the previous owner added the addition of the guesthouse and did some weird things with the roof. The dishwasher was new and installed by the retailer so I don't know if it has to do with the roof or with the dishwasher.
@Will Fraser Thanks for the advise on the roof. I'm contacting a drafter in the area to get some drawings. That way I can get more accurate estimates from contractors. The roof is old, and it has new"ish" shingles on it, but it needs new decking and not just the part that gets reframed. My GC said he had roofers and they could do the roof after I got it rented out, but working was him was such a mess that I didn't want to use him again. When I talked to my insurance company - I told them roofers came out and said there was hail damage - they said they would only cover actual cash value. One of the 3 roofing companies that looked at it advised me not to involve the insurance company until I had the cash ready to fix it because they could determine it uninsurable and give me a short timeframe to get it done. Based on that information, I was planning on talking to my insurance company more in depth a week or two out from when I have the work scheduled.
Here's a photo of the roof. The guesthouse was added by the previous owner (pink door) and then an extra section at 7:00 from the the circle. I circled the area where there is mold behind the dishwasher and then on the ceiling in the utility room (utility room is directly under the guesthouse and a flat portion of the roof where the window is in the middle of the circle). I also noticed some pink mold forming on the utility room walls that those exterior stairs are attached to. There's no roof attached there so I'm wondering if there is an issue with construction of that wall. I removed that odd pile of bricks and also a bunch of roofing shingles under them. Looking back, I now wonder if they were placed there to conceal or hide something.