If you time this well, and develop mid-late Recovery phase, your projects should be coming online right at the height of the demand depending on the market.

There are still a few pocket areas of the Oregon Coast that do not have any restrictions, many where active rental permits transfer to the new owners, several where the allocated number of permits has not been reached or where there are very reasonable waitlists for a new permit (often in the single digits.) 

It’s a heavy tourism area with year round demand and tight restrictions on STRs that keep room rates high.  

Supply and demand is very high right now because people are moving from outside the FL to here because of the what type of restrictions the COVID virus has caused in other states.

There are lots of restrictions but these are extremely common out here.

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 only way to legally operate one is a true owner occupant, and even that has some restrictions.  

We wanted a beach house for a long time, Florida seems problematic lately with raising costs and tightening str restrictions.  

The garden unit is nice, finished, has a kitchen, and 2 bedrooms+1 bathroom, 2 egresses, stairs connecting it to the unit above as well as an exit to the outside but ceiling height is 6'5". 

Cleveland was hammered in 2008 and prices are getting back up (in some areas) where they were at in the early 2000's (Shaker Heights, Cleveland Heights etc.)Other pockets in the city that were historically distressed are now seen as areas to collect cash flow as investors are renting them out via long term as the cities rental population is nearly 3/4's of the population.