Properties seem to be pretty inexpensive.

The local store may have a limited selection but you can find more sizes and options on their website.The tenant may very well trash them, but they are inexpensive and can easily be replaced with the deposit.

It's on the inexpensive side, but between the survey (about an hour) and screen-time, it takes me about 6 hours.

It looks like reverse 1031 is better in terms of timeframe.

From a management position, Evan is correct in that most issues are dealt with on a business hours timeframe vs. 24-7 for anything residential in nature.

@John BertolonIf your goal is to have tenants move out so you can do renovations I'd hold off on doing upgrades unless they lead to higher rents.However, if you want to keep the tenants and the repairs are inexpensive and beneficial long-term, it’s worth doing because vacancies will cost you more.Replacing items like appliances can be costly, so if they're working well, I wouldn't address those kinds of requests.

Labour is inexpensive but what may take 6weeks in North America, will take 10 weeks in the Caribbean. 

You also have $30k in unreimbursed expenses.If you are smart, you pay off the HELOC and reimburse $25k in expenses.

Secondly, they are high touch rooms meaning they receive a lot of use and buying inexpensive materials will breakdown quicker. 

(I'd be moving to another primary residence so I'd end up with 1 primary and 1 rental still, just a bigger more profitable rental with almost no mortgage) If I did this, what would the time frame look like - how to I "prove" it's a rental now and not my primary?