Treating property management as "passive" income lowers the bar on professionalism and hurts both tenants and properties.

Initially, we plan to invest in lower-risk opportunities such as arbitrage to gain a better understanding of the market.

You also have the option of paying NO capital gains if you sell it within 5 years after move out.

Numbers in FL are not looking great with insurance/taxes/HOA fees/etc for cash flow but willing to  focus more on just breaking even (or close to even) and having significant long term appreciation.Option 2: take the cash, pay 20% long term capital gains and wait as market continues to dip for a prime buying opportunity.Would greatly appreciate insight/advice from those much more experienced and knowledgeable than myself.

Hence, they are looking at STR as business income rather than passive income.

As a result, I'll be selling my house and using the gains to put a down payment on a secondary house next to my current rental property.

IRS Publication 537 outlines installment sales (seller financing), which, depending on the seller's individual circumstances, can defer and sometimes reduce the amount of capital gain tax owed. 

If you don’t have the right temperament and sufficient cash reserves, you should consider selling the property and investing proceeds in passive type investments. 

If you or anyone else has personal experience with quantifiable evidence of successfully owning a small or medium size business on an absentee/passive basis I would be interested in learning about it.  

Hi Monique,I'm a local rookie investor and had tons of inspiration and knowledge gained from networking with other people, podcasts and reading tons of material.