Probably good to have one or two of these started early rather than later since the the premium will increase as you age due to health/age.

Whether to jump in now depends not only on interest rates but several factors including where you are financially, do you think values will increase or decrease over the next 2-5 years and will the investment provide you with a better return than investing the $ somewhere else.?

Keep monitoring the rents in your market, make sure you are taking advantage of any increases possible, but don't get too greedy if are happy with your tenants. 

If you were to self manage that would increase your cash flow but that's another level of time and risk involved and if you're doing it out of state I certainly wouldn't advise it. 

Ft Myers has been stable and steadily increasing rents.Cape Coral was decreasing rents for several months but stabilized.

The thought of short term rentals attracts me.

Thanks to the Cost Segregation Study, the property investors were able to reclassify the property components and accelerate their depreciation for a total of $356,000 in the first year.The use of the accelerated depreciation strategy helps real estate investors to reduce the tax liability immediately which therefore increases their bottom line due to the offsetting of income.

The primary reason to leverage the asset is to increase your returns, or diversify your holdings.

Alternatively, you can opt for other strategies like STR, MTR or rent-by-room to increase cash flow. 

Listing inventory looks to have a trend that is counter to most other markets in Massachusetts; usually inventory increases in the Summer and lessens in the Winter!