I don't know the ins and outs in IN, but in NJ its a pain if a structure is dubbed a 'historical landmark'.  

Often short term pain (like reduced cash flow) will pay off in the long term, as you pay off 30 properties within a couple years, but you don't see the benefits until 20 years from now.

The live auctions here are a pain in the ***.

I haven't gotten them to underwrite at a lower interest rate though, and that has been one of my biggest pain points with them. 

Sleepy markets, or worse, markets where people are moving FROM, are likely to inflict the most pain or at least present the most challenges.

I do understand that there is some growing pains to be expected with any new tenant, however, 13 service requests in 6 weeks seems to be a bit excessive.

Pensions Cut etc-Realtors can be a pain and snitch............

My part time job is working at a medical clinic doing pre-employment drug screens for contractors coming here to work at the refinery, a good way to meet potential tenants  My wife keeps the STRs clean, that's her full time occupation.

I have a very detailed spreadsheet, but its a pain in the rear to instert receipts and invoices etc to tie it to all of that and requires a good amount of work every month, which is why I am looking for something a little more user supportive

Let them know what you want, that you will not be a pain, second guessing client, and that you can close with out issues.They can/will call you with properties that are not yet listed as soon as they get the paperwork signed.