The truth is owning property is a pain in the butt, if it's not a good deal that cash flows, there's really no point in having it. 

Yes it can @Kenny CharlesAs long as probate has started and it's during the administration process that negotiations can begin. 

When I am dealing with a pain in the butt contractor or tenant those are the days I really am sick of it, when the rent check comes I am obviously in a different state of mind.

Ending up pain 3 times more during that time to get it fixed by a professional that's if you can get a hold of someone.

If they refuse, suck it up and go through the painful process of eviction so it's on their record, you get a judgment and (maybe) get some money back, and both you and the tenant learn some valuable lessons so this doesn't happen again in the future.This will teach you a valuable lesson that (hopefully) will encourage you to be more vigilant in screening and lease enforcement instead of letting problems get so bad that you have to evict.

I definitely dont want to possibly have to go through all that pain in the butt to end up only getting back one of the properties in a worst case scenario!  

It would be a pain to be having to move everything from room to room.

The first deals are slow, painfully slow, and then if you treat people right and keep consistently working, you end up with more opportunities than you can juggle without scaling up.

When looking at investment properties, sometimes I come across ones that have tenant at will, usually long term tenants who are paying way below market rent.How do you guys handle these situations to try to bring the rent up to market value in the least awkward/ painful way?

Dealing with the historical districts is a HUGE pain in the butt.