Repairs, are what depend on being "placed in service".So ultimately, (you assume no liability here for tax advice) best practice is to itemize receipts so that at the end of the year, it's easy to determine what was a repair and what was an improvement.Currently I have a lump sum figure, not itemized.  

Have you already read the Ultimate Beginner's Guide?

We have had a couple situations with repairs that we believed were the tenant's fault, but ultimately we took responsibility for paying. 

Ultimately, I decided to self manage for the learning experience and cost savings. 

I came across a lot of videos by Brandon Turner and most of what he said made sense, so I figured I'd do more research about BiggerPockets which ultimately led me to join the site. 

The LLC is a pass-through or entity, so it is ultimately recognized as part of my single tax return.After all factual and legitimate accounting, the tax exposure can be significantly minimized with proper planning, documentation, and execution.Again, I’m not a tax professional and I don’t play one on TV.

Having said that, I'm trying to approach this using @David Greene's model of finding 2BR units with 1000+ sq ft in an effort to buy low, convert into a 3BR, then ultimately cash out refinance.

It definitely depends on the servicer and who ultimately backs the loan. 

The agent or PM doesn't have the ultimate say on the rental criteria.

Sounds you just answered the question with the ultimate question:time v money