The biggest concern is make sure that they do not continue to pay or not pay the rent according to their wishes and abide by the terms of the lease.

The UBIT is the biggest kicker for me, even though it would probably be less than the taxes on the early distribution I would still have the ability to pay back the distribution over the next 3 years if I want... unless I can use the accelerated depreciation to offset the tax liability. 

But with maybe 15 year service life here in FL, age really isn't a factor for these unless your looking at brand new builds.The biggest thing to consider, in my way of thinking, is the neighborhood.  

Great additional source of revenue and pet-owners typically stay longer leading to less turn-over expenses.Not sure about in a short-term rental, but as long as you have addendums for pet damages, I wouldn't think there'd be too many problems.

My biggest regret was not goi g all in back then.

As a real estate investor, I would lean towards the multi-family purchase as it allows for increased revenue stream and greater returns.

Hi @Ryan Sullivan, I'd say the biggest determining factor in this is your market. 

If I could just add one more thing, I'd say that one of the biggest benefits of putting your properties in a living trust is that everything will pass to your heirs without having to go through the probate process.

This would be the biggest project I have tackled and only my second rental.

One of the biggest factors on insurance premiums is something called an insurance score.