Hi Randall-Congratulations on buying a rental property well back in 2020.I am sorry to hear the property is now cashflow negative $200 a month.Your question is should you sell or continue to keep it with the negative cashflow.Depends on your personal goals and if being negative $200 a month plus any unexpected repairs or vacancies is affordable to you, but if you can solve the negative cashflow by turning the property into a furnished mid-term rental, for example, your future self may thank you.To Your Success!

Not many folks can afford to buy 5 properties with a working business.

Once you have a consistent amount of income from your business for 2 years where you can afford to buy a primary, then I would look into house hacking.

My rents are high at $6300 per 3BR unit so I guess the risk is if economy goes south and no one can afford the high rents.     

Given that affordable housing is a national issue it seems that the more pathways to home ownership is a good thing.

Studies typically cost $3,000–$5,000 but affordable DIY options (around $400–$500) exist for simpler properties.

@Priscilla C. how much can you afford to put down without tapping the equity in your current home?

I guess the only thing giving me hesitation is that it looks like housing prices are at all time highs even after adjusting for inflation:https://fred.stlouisfed.org/se...Housing affordability is worse today than it was at the bubble peak in 2006 if you believe Case Shiller data. 

In some markets you can afford to increase more and in some less.I raised my tenants rent by $15/m and they were ecstatic. 

And the condo debacle in FL will be churning for quite a while as these rogue HOAs try to get realistic with deferred maintenance, new requirements, and freedom for people to use as they need to afford them.One thing to consider would be to 1031 all of them in a consolidation exchange.