Appfolio (what we use) is a pain to set up but like you, once it is set up, works great.  

This has probably been the biggest pain point for me looking at deals online and not knowing if I can improve the properties to raise the rents. 

It can be a bit of a pain to remind and chase after water bill on a quarterly basis however, I personally recommend keeping the bill in the owners name.

I never believed I would feel such pain without having my children in the same house as me.

Declining population, higher than average crime and low income levels are all the factors that will surely lead to a lot of ache as a landlord and potentially no appreciation in the long run.

Honestly even though its a huge pain I understand the lender wanting to make sure you live in it if the type of financing you are getting is based on living in it.

And to think like an investor, being one is a great way to learn what is important, how things work, where pain points are, etc.Your best bet is to talk to a securities attorney.  

You have to notify tenants within 30 days if you're planning on keeping deposits in IL (https://www.ilga.gov/legislati...).It feels like the tenant is trying to pull a fast one here, but security deposit management is quite a pain.

Larger apartment complexes and multifamily buildings aren't as common, and demand for rentals is usually pretty strong.The major issue you may run into in the future is if you get a larger portfolio, it will likely be a long and painful process to liquidate should you ever decide to do so, since putting ten or twenty houses up on the market all at once in these communities would probably add 30 - 100% to the available inventory, greatly reducing their potential sale price.

Apartments dot com has been a real pain point so far.