What are the pain points for expenses?

I don't think you can compare: (1) The pain of a tenant with a job who's paying the full amount of her/his own rent for an affordable place that's suddenly not affordable at all, to (2) The pain of an unemployed or minimally-employed tenant in a similar place with a housing choice voucher, to (3) the pain of a tenant in a B-class place who's choosing to pay a fair bit more for X, Y, or Z reasons.It's amazing how the poor people who do their level best to play by the rules and pick themselves up by their own bootstraps always get shafted the hardest in America.

Its OK to get one for psychological reasons don't get carried away on thinking your safe just because you have one. 

@Kathy Henley gives you a good road map for delaying your decision pain free.

@Dylan Grieve - Thanks for sharing, even if it's painful.

Understanding the psychology of it all will help you tremendously. 

So, build as many relations as possible and understand the pain points of sellers.Conclusively, we should widen our market when we have dived in deep into the current one first and have developed some quality relations!

I use Apartments.com for payments and it's kind of a pain (especially when a tenant gives you an incorrect e-mail address - long story) but they don't charge for ACH payments which is nice (though it takes almost a week to process). 

Paying a bunch of lender/ closing fees twice It’s one of the pains of the BRRRR process

The resident that know all of the rules of the leasing game, what you as an Owner can and can't do, and actively seek to be a pain in the rear.