For me finding handyman/contractors to do the make ready has been my biggest challenge for out of area properties.

I think the biggest thing is that it prevents us from buying a house in an area we’re unfamiliar with as a our long term home and is end up hating the area we buy in.

The biggest takeaway from what I learned is that people are investing in you more than the actual deal.

The biggest danger is hidden structural damage.

I've explored the cost and the requirements both personally and professionally as a site and land use civil, and the biggest savings is in reduced construction time.

Now I haven't been in the STR game for long, but I do happen to have the largest portfolio of long term rentals in the Cleveland market so take this for what it's worth.....Some speculation based on some semi related experiences being the biggest name in the game in regards to LTR's.To me a lot of the problems you are encountering are a direct result of what type of property you're renting out.

One of the biggest questions is - what is your long term goal? 

Hi Becky, In my opinion the biggest differences for landlording in MA and NH are taxes and regulations.

Although I attribute my kids to why I bought rental so maybe if I didn’t have kids I wouldn’t have rental idk.I am getting ready to start my first out of state deal and I think the biggest think for me is the contractor.

There are many brokers who are geniuses and blow me away.The problem you have is; you have to read to re-read all the above to cover what I need to say.Your biggest hurdle is whether or not you can do some simple math, but the math is not simple in the sense that it takes a few minutes.