Best bet is to get inspections and or professionals out to assess the systems and provide estimates.With the roof 20-50 years depending on the climate, area, type of shingle and type of roof.

Not climate controlled.

I am thinking about buying a vacation rental in a warm climate (Florida, the Caribbean or Central America is what I am considering) as both an investment and to use for my family for a couple weeks out of the year.

As an out of state investor I prefer warmer climates in more landlord friendly locations.

It may also decrease value in cold climates. 

Such as: Post #1:  Looking for insights into the current STR regulations climate in Palm SpringsPost#2:  What is it that I should know about investing in Vacation Rentals in Big Bear that I'm not thinking about? 

Yes Nick, I realize this is a numbers game but I was just wondering with today’s climate and markets, was there any method(s) that seemed to be working better. 

I live in CA and due to pricing and the regulatory/landlord rights climate did not want to get involved here.I went to Kansas City MO with the plan to buy our first home through a highly recommended turn key company.

Are both viable options given current market climate and locations of interest?

I’m new hear. I am soon to be buying a set of 8 duplexes for $185k. Rents are currently at around $200-$225 per and this is the only bad spot in this side of town. Currently 13 of the 16 units are rented out.  I am a ...