I think with the subsidies and if you have good exposure, I see no reason why not to do it.I'd just make sure:1) It's professionally installed since poking holes in the roof not good2) See if you can get some kind of workmanship warranty in case you do get moisture invasion3) Find out what gets recorded against title.  

As mentioned, the freeze/thaw cycle combined with moisture can be a problem with it on the front range of CO.  

I would also take a moisture meter around the rooms in possible spots of spraying or missing the litter box etc.

Provide paid invoices with dates to prove the moisture intrusion and related repairs had taken been completed well within the 30 day mold remediation period.Provide copies of all tenant emails related to their claims.

By caulking the base, WHEN there is a wax ring leak, the moisture will sit on your subfloor, which is exactly what rots them to begin with.

I'd spend every dime you have on a replacement roof, HVAC repair/replacement, moisture control, and then tackle a kitchen or bath if the budget supports it. 

Again, something your insurance agent is going to scrutinize.100+ year old houses tend to have dirt floor cellars (or crawl spaces), so moisture is a thing in the house. 

This will let you know if there are any plumbing leaks or any clogs in the sewer lines.2nd look at the foundation very closely, look for any stress cracks and see if any moisture coming in.3rd check out the HVAC systems.

That stated, I'd sure like to find out why the OSB failed from moisture issues as it's supposed to hold up to weather.

Well they make their money selling moisture barriers and whatever else.