Being from Chicago, I'd tend to agree with you @Craig Jones those areas of Wisconson and & Michigan are driveable from a lot of those metro areas you mentioned, but I think the toughest part of any northern short term rental is the seasonaility. 

However in the future because  of how these things tend to go, I would not have called insurance or a remediation company, I would have just fixed it immediately before it got too bad then warned the tenant not to do it again (and to be fair to them it’s odd that simply hanging a picture would cause a major plumbing leak, the likelihood of that happening is so low) and moved on.

Of course, with all things, the answers to all these matters will depend on the circumstances.California tends to have more laws on the books and requirements and restrictions that it can be a good idea to form a CA LLC for out of state property so that you as a CA resident are covered, and to try to have your contracts fall under the purview of CA courts.

Of course, with all things, the answers to all these matters will depend on the circumstances.California tends to have more laws on the books and requirements and restrictions that it can be a good idea to form a CA LLC for out of state property so that you as a CA resident are covered, and to try to have your contracts fall under the purview of CA courts.

The quick good/bad of Section 8:- S8 tenants tend to be rougher on the property (but not always)- Paperwork/inspections/etc. can be burdensome and tough to navigate (especially initially)- People often think FMR rates are guarantee rental rates but that's not the case- Usually the rent isn't 100% subsidized and a lot of people don't realize this- S8 tenants tend to stay a lot longer than cash tenants- Obviously, the guaranteed rent portionOverall, I'm neutral on the program.

Also, we can be relatively sure that they won't overstay without permission, as we tend to be fully rented for a year or more out, sequentially to 3-4 separate individuals.

I tend to pay back within 6 months, so my score bounces up pretty close to the original score after the final payment is made.

I'm sure the answer is "it depends" but in general, do people that operate medium-term rentals tend to find a better response from a unit that looks pretty or a unit that might have some more perks while someone is there for a short time?

As a fellow Northerner, I tend to buy in the Southern half of the US for 2 reasons:1) you get much higher year-round occupancy rates in the South & it’s simply tough to earn a good ROI in the North if your place sits vacant for a big chunk of the year2) Culturally, the Southern half of the US seems to be a lot more accepting of STRs regulation-wise.

Each market has its quirks; like, San Antonio is all about maximizing cash flow, while Austin tends to be more of an appreciation play.