Condo's are usually on the cheaper end of cost for appraisal reports, typically not $750 (but if it's a high end condo or in an area with there's some complexity, the fee can reflect that). 

@Zach Howard if you're serious, you'll get a Pro Membership so you can access the analysis reports here on BP.You can then share those and ask for feedback:)

If you only have one LLC and don’t need entity tracking, you could get a lower subscription and categorize your properties as ‘customers’, then units and tenants would be sub-customers.Simple Start would allow you to invoice your tenants (if desired through QBO) and produce basic reports. 

I have talked to a few Hedge fund managers who like the concept of the Sub to, makes their product more investment worthy to not have a bunch of non preforming loans to report.

@Brandon SturgillDealCheck has a complete built-in glossary with explanation of every term/metric, including the exact calculation formulas used.

That would be a helpful addition to your plan as you would further reduce your cost of living.Also don’t forget from that $600 you are planning on getting in cash flow you have taxes, insurance, maintenance, capex, and vacancy to consider.With two homes, you may want to keep that extra $20k as an emergency fund rather than spending it on a third property and then be left with no emergency funds.The $1,000 a month includes incidentals for maintenance and taxes etc.

Get a signed bill of sale including the furniture at closing for tax depreciation.Communication is key! 

There will likely be a partnership return required where you flipped a house with a partner and lost $120,000.If you sold the other property within the same partnership, it will also be reported on that partnership return.The net result to you is that you will receive a K-1 showing your income / loss which you then use to report on your individual return.If you made no money within the same year, you likely pay no additional taxes / get no additional refund.Best of luck.

@Bryan Stengel, I think alcohol has been the tough one with the STRs, not sure about if you need license( hopefully someone will chip in ) , however there  always the liability part including but not limited to offering alcohol to people who are trying to quit etc.

My primary focus is on properties in Miami and the surrounding areas, including Homestead, as I’m familiar with the market here.