Anyone heard of services like Choice Warranty that take care of any maintenance items for your houses like heating/plumbing/sewer/water issues/appliances, etc.?

The later choice takes times and rarely bears fruit in our experience. 

I estimate 350-500K in repairs and the ARV based on conservatives numbers at 8% cap is around 1.6 million.I have been "winging" it on my previous buildings to an extent but all of them turned out great with excellent cash flow and big forced appreciation. 

Any platforms that allows to keep track to have this at my fingertips in an app that isn't an Excel spreadsheet?

They can definitely be an excellent resource for these sorts of questions too. 

Your choice is to go along with the scam Tenant A started and work with tenant B or get rid of tenant B is MA currently allows you to do that. 

If you're familiar with Microsoft Excel or Google Sheets, those are going to be the easiest solutions to build a customized tracker for your portfolio.

My advice is tell her she has two choices.

If you have not purchased the book, it is excellent and dirt cheap at $12.99 so it should be on every landlords bookshelf. https://store.biggerpockets.co...I also recommend the book Landlording on Autopilot, which also has forms download.

Here short term rentals are very seasonal.As a newbie, I was under the impression that buying a brand-new apartment would be the right choice for me.