You must work at least 750 hours per year in a qualified RE business.So most people who have high-earning W-2 jobs outside of real estate won't qualify.But the unique thing about RE pro status is that even if you don’t qualify but your spouse does, you can both file jointly and claim the losses from your RE investments to offset your other active income together.It's an incredibly powerful benefit if you do meet the criteria.

If my goal is long term hold and passive cash flow, it would seem the 721 would offer even more diversification.

What income streams do you have besides REI, or is this it?

Active vs passive. 

For investors, the current market presents a mixed bag: while short-term rental income may be lower, Miami remains a strong market for long-term growth as affordability attracts more tenants.What’s your take on Miami’s rental market?

Quote from @Brandon Croucier: Financing a commercial MF that runs as an STR is possible.Appraising a property based on the income is not, whos to say a buyer would STR the property. 

You'll have to look at the income and expenses to predict whether your cash flow will improve.

You may not need to visit each property you buy in that area though.4) Unless you are buying Class A turnkey, you should have a PMC.5) See below copy & paste info:-----------------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

- Loss of historical data (for both IRS audits and for personal portfolio tracking.)You should be able to print the general ledger and Balance sheet / income statement for each period.

Very nice, what is annual income?