Personally, I like to use Notion for this type of task, but I'm sure there will be others on here that will recommend Monday.com, ClickUp, or Asana.

Or hire a PM company to manage for you?

I also have a personal relationship with my contractor so got a massive price break. 

Just ask the person straight up how they rate themselves in terms of looking after a home and what they say and the nonverbal cues will likely tell you what you need to know :) 

If you’re looking for more insight on RRG or your particular STR deal, I’d say most people on BP would agree that I’m the go-to person here for that.

It took some digging, working closely with a title company, and negotiating with multiple parties to get it resolved, but in the end, it was a great learning experience—and a successful deal!

Can you send me a link and/explain from either personal experience or an example of when you seen that happen.  

Think about an HVAC, storm damage, paying for housing if a tree falls on the roof, dealing with stupid insurance companies, etc.

I'd personally sell the townhouse (doesn't sound like it cashflows or would make a good rental property) - you may have no capital gains if you have lived in it the past 2 out of 5 years - I believe the first 250k for single filers is exempt from taxes and the first 500k for married couples.

If you need a conntection in Upstate NY I can direct you to the right person.