I invest regularly in Worcester, Providence, and towns outside of Worcester. 

Banks do this regularly during any kind of financial hiccup.  

That will help keep thing square with the guests.Remember that you need to do a full background check etc etc with a regular full lease for the time they are there.

Whether it was regular depreciation or bonus depreciation from cost segregation - same treatment basically: no immediate tax consequences. 

I'd like to invest back home in Ohio eventually (I lived in both Columbus and Dayton for about 5 years each), but I'm much more comfortable starting with something I can see regularly. 

If you do that, it goes on Schedule E like a regular rental, but the difference is that the tax loss isn't limited by the passive activity rules on form 8582.

I have been doing that since September.The resort is beautiful and the proximity to Disney is great.For someone that wants to travel to the parks on a regular basis owning in Margaritaville is perfect. 

Here is the summary if you are interested.In this case, the main question is when did the investor completed his start-up phase and became actively engaged in his business.Whether a taxpayer is engaged in a trade or business is determined using a facts and circumstances test under which courts have focused on the following three factors that indicate the existence of a trade or business: (1) whether the taxpayer undertook the activity intending to earn a profit; (2) whether the taxpayer is regularly and actively involved in the activity; and (3) whether the taxpayer's activity has actually commenced.

My family member owner regularly receives (non-specific) offers to buy the apartment building so I definitely think the buyers are out there for something like this.Any thoughts about apartment building sales would be appreciated!

But classifying your depreciation (either the leftover annual depreciation after taking bonus depreciation, or the regular amount of depreciation if you didn't take bonus depreciation) can be taken as an active deduction against your W2 income for as long as you materially participate in the property.Disclaimer: I'm not a tax professional so not financial advice.