(A long overdue) Update!
Wow, it has been about 6 months to date since I last updated this thread. Time to catch up!
1. The Roof
To make a long story short, the roof still hasn't been replaced. I wasn't able to get anyone under contract to replace it before winter, and the material shortages paired with the sudden bizarre demand for contractors in the spring has made it damn near impossible to get any contracted work done without a months long waiting list.
I did finally get someone signed on for the project though, and it was not the amish crew I was planning to go with back in December. I got an updated quote from them in the spring and the price had gone up from $12,000 to $14,000 due to increased material costs. I called up a guy that my step dad recommended (step dad works at a building supply store and knows all the local contractors), and immediately got a great impression from him. He's Mennonite and has been in the roofing business for about 20 years. I've heard from numerous people that he does the best metal roofing in the area. He quoted me $16,000 for metal roof, and that includes tearing off the old shingles and replacing any damaged structural boards. I know that a lot of people here and elsewhere had been strongly opposed to putting metal directly overtop of shingles, so the fact that this guy was so insistent upon tearing the shingles off first made me feel a lot more confident in his work. As such, I felt it was worth the extra $2,000 for the peace of mind that comes from knowing a job has been done right. He is of course extremely busy and booked out for months like everyone else - he says he expects to get started towards the end of summer, likely late August or early September.
The roof did spring a leak back in April during one particularly heavy rainfall, but thankfully the guy I contracted to replace the roof (we had just entered into contract a few days prior) offered to come out and patch it free of charge. There have been no issues since. Fingers crossed that remains the case until the new roof goes on here in a couple months.
2. The Holdover Tenant
There is a lot that could be said here, but I'll do my best to summarize. The short version is that the tenant formerly known as squatter is now presently known as inmate. The slightly longer version is that he stayed consistently about a month behind on rent for the 5 months I had him, then on May 22nd while I was at work he allegedly got into a dispute with someone and pointed a gun at them through the window of his apartment. Police were called out and found multiple unlawful firearms on the premises (he has a felony on his record and as such is not allowed to possess any firearms). He left that night in cuffs and probably won't be out for a very long time. He's looking at anywhere between 5 and 50 years, depending on how generous the judge feels like being. He willingly relinquished his tenancy, and his family came by and got all of his stuff within 2 weeks of him being arrested. So he is officially out of my hair, and in a manner that was much easier for me than I was expecting.
So now as it stands I have two tenants (I did place a tenant in the one bedroom unit but they will likely be moving out at the end of September) and one vacant unit, which doesn't need much by way of renovation but I want to let it sit empty for a month or two just to make sure the next tenant doesn't end up getting any visitors that are former associates of the prior tenant who was evidently mixed up with some shady stuff.
As ever the Great $45,000 Triplex Saga continues to be a wild ride, but the future still looks quite promising!