Am I potentially exposing myself to some sort of issue here?  

It may limit your property manager's ability to select the best tenant.

To avoid going through the same poor experience, keep reading.Even if someone gives you a referral here, do NOT make the mistake of assuming that the PMC will meet your expectations, just because they met the expectations of the referral source.In our experience, the #1 mistake owners make when selecting a Property Management Company (PMC) is ASSUMING instead of CONFIRMING.It's often a case of not doing enough research, as they don't know what they don't know!

We use buildium accounting for our units -- it was one of the reasons we selected buildium.

If there's selective demo that's required after the initial demo is completed for the electrician, plumber and HVAC tech, do you wait until sheetrock is hung to have it cleaned up?

It ended up getting sorted out and the rent got issued through the CHMA, but there WAS a delay.

When you select the next tenant I would certainly ensure that you have your eyes on the applications that are coming in, and ask that you are involved in the decision making process. 3x income, clean credit and background checks should be a minimum for approval, even if it takes a month or so to find someone. 

I have a CPA I work with who I’m sure will sort all of it out, just didn’t want to do something if it would cause a huge tax headache later.Do you know if you convert a STR to a LTR after a cost seg, will it cause a large repayment of taxes (I’m doing the cost segs to lower my W2 tax rate).

My suggestion would be to select someone with the most forum posts or most reviews.

All sorts of little things you know if you are local but hard for outsiders to navigate.