It's a modest start: a $50k condominium that we purchased for cash in need of only moderate cosmetics.

My ultimate goal is to maintain a moderate lifestyle through passive income through rental properties and as a hard money provider.

I really want to grow within a moderate risk tolerance, where debts are covered and there is still positive cashflow even at the worst of times. 

Plus people need to get away and relax more when times are bad, that's why alcohol sales always go way up during tough times.....

The robot moderator deleted the post because they thought it was marketing- they never read the context of the post but just delete because that's what they can do. 

A fair and moderate approach to all things landlording will serve you well. 

The term “transient accommodation uses” includes but is not limited to hotels, motels, recreationalvehicle parks, tourist lodging facilities, resort condominiums, resort dwellings, vacation resorts, and dwelling units occupied or available foroccupancy on an interval ownership or “time share” basis, when any of the above are made available for occupancy more than three times in anyconsecutive 365‐day period and the right of occupancy is for a term less than monthly.The term “transient accommodation uses” does not include any of the following uses if such use otherwise complies with the applicablerequirements of the City and is licensed by the State of Florida, if such licensing is required by law: bed and breakfast homes, community residentialhomes, nursing homes, rehabilitation facilities for persons with drug, alcohol, or physical impairments, respite care facilities for persons withterminal illnesses and their families, short‐term/emergency housing or long term housing where allowed by this chapter, and child foster homes.The term “transient accommodation uses” does not include a guest house dwelling, when one or both of the sleeping rooms are located as apermitted accessory use within and incidental to the primary residential structure and the primary residential structure is owned by a naturalperson and occupied by the owner.

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We own a home, so I don't know if house-hacking would be right for us.I am moderately handy, so flipping may be an option.

You just have more crime there than other residential neighborhoods because you've got all the bars (alcohol, drunken fights) and a larger percentage of the homeless population which represents a decent portion of the violent crime there.See: Who is to blame for ‘aggressive behavior’ by homeless people downtown?