The carpet and counter tops will be my most difficult ones to work on.

It is sometimes difficult because I only get maybe 2 minutes to talk real estate then have to stop.

My mind works that way too.In my experience, whenever I've truly wanted to learn a new business inside and out (especially if I didn't know anything about it to begin with) I've found that it's very difficult to completely cut out the less exciting aspects of the business and whittle everything down to a short list of bullet points.There are definitely a lot of "quick start" guides out there (and they're great for highlighting the biggest action steps at the outset), but there's still a lot of learning that needs to happen to fill in the gaps.

It is kind of difficult to decide since I need to move with my spouse and 3 yrs old daughter.

Some municipalities can be more difficult to work with...As others have mentioned, your mileage may vary and anyone can be good or bad.

Oregon STR's are a limited asset class and likely to be more difficult to acquire during the next 2-5-10 years. - Comparative Affordability: The Oregon Coast still offers a lot of value in comparison to other coastal states, particularly neighboring California & Washington.

I am in the same boat and completely agree with you in that the rental market does seem to be changing quite a bit in recent times- much more difficult to get good qualified tenants these days and decent tenants seem to have their pick of the litter - often very flaky and uncommitted because there is so much supply out there.Rent price is definitely a key issue but what's the more likely outcome of a significant drop in rent price below market?

@Mark Jajowka It is getting difficult to place insurance if the building has an older roof.

Certain property types can be more difficult to finance than others, one of the more difficult to secure financing for is multi family or mixed use properties above four residential units. 

It's very difficult to simply build affordable housing, but perhaps older housing stock can become more affordable as new housing is introduced.