if you are looking for advice, you are in the right forum. start reading and grow

Replacing the roof is just the start.

We plan on starting renovations on the unit in X (I would say a date but in reality have a 2-3 month buffer), and based on this we are no longer going to be renting the unit out.

One year from time of payback or time of loan start date I’m not sure of. 

Start niching down now, master your chosen property type, and don’t pivot until you’ve got it dialed in.3.

@Stuart Udis, I think there is starting to be a bit of a shift here.  

Quote from @Will Greenlee: I would agree with @Drew Sygit every software has its kinks and this one along with all the other ones started somewhere.. 7-8 years ago Buildium was less effective than it is today, and now it is a lot better.

Stay consistent and things will start to fall into place

Started using Xero last year, as better bookkeeping was needed a new acquisition with a partner. 

I think when you start you need to make sure you work with people who are reliable.