Sure thing.
This type of thing is going to depend so much on your personal situation but here's what I experienced and I think from what I've discussed with other people, its pretty typical for the most part.
-When you buy a place like this, usually it is going to be in a place that isn't right down the street. If you live in a city neighborhood, most people are looking to buy beach homes, cabins, country, etc, for example. So that brings up the issue of convenience in getting to the place to do the work and oversight it needs, worrying about not having a set of eyeballs on it, etc. If you buy a beach house, for example, believe me, you will become very familiar with every storm blowing near your beach and you will either A) worry too much about it, B)spend too much time correcting things going on with it, C)paying someone too much to do these things, or D)all of the above.
-A lot of people (I was one of them but I realize you may not be) buy places like these and they have this very exciting idea and visualization of what this dream place that you've wanted for so long should be. But then you are faced with the reality that its not easy to do these things when they are far away, financial issues are involved, and definitely (definitely) when you rent it out because no matter how you set it up, other people will simply NOT look after your place the way you will and it will bother you.
-Which leads right into the next layer of the rolling snowball. IF you are married or partnered with someone who loves the idea of this place like you do but who is also a person who has high standards, it becomes miserable. My wife is organized and thinks people should be respectful of others' property. She has high standards for cleaning her home. So when people rent out a place like this, its a frustrating and disappointing prospect when we would travel there because it was never maintained well enough. There was always something not cleaned, always a new ding or scratch or tear in something. It just wasn't fun to spend half your time doing stuff to get it to where you would enjoy it. I know not everyone is like that but if you or your partner (or both) are then you will end up instead of having that visualization of what this place was going to be and you being able to comfortably slide in with a few bags packed and just enjoy yourself on that comfy cabin couch to....buying cheap furniture you don't care if get destroyed because nobody will take care of it and you end up feeling like you are settling for much less. I hope that example makes some kind of sense.
-There are a LOT of "not easy to see" costs associated with owning places like these and even if you are on top of things in trying to make it work out a little better at tax time, it just becomes a lot of work.
Its just lots of little things like that and they go on and on and pop up all the time and you just don't have enough control over the situation to reasonably plan it out. I have been a landlord (local and not) and this was more frustrating than that. In the end, we wound up just buying a couple of weeks timeshare for the beach experience. The weather and maintenance of ocean property is grinding. And we did end up with a cabin in the middle of nowhere in the woods but we NEVER rent it out and we found that to be a much better option for us. Everyone has different levels of tolerance for these things but like I said I have found that my list of "gripes" seems to be fairly common with a lot of people and we seem to have a common denominator that we kinda thought about them beforehand but it wasn't the same after we experienced them for ourselves.