I am debating if I should buy a decently priced home in Florida using a mortgage, rent it out as soon as possible, and have a tenant(s) pay down my mortgage until I am ready to move in and have the mortgage either paid down or nearly paid down.

I decided to buy the house in my name to qualify for a homestead exemption.

Not quite on the level of SBF or Madoff buy up there for our industry. 

Hi, I am based in MA but about to buy rental property in NY.

@Bridget McGingAt some point, you have to just do it and buy the first STR and learn as you go.

And here is a video that helps understand how to get the 100 hours for material participation.Another way is to buy a property in a company name and utilize section 469 grouping activities.

The best way to protect yourself investing in NYC is to buy higher quality assets and require exceptional credit credentials from your applicants to obtain approval to rent.

My mom sold her house and downsized and rather than buy a rental, she put the money in a savings account.

Buying an existing place that needs upgrading might be more sensible but it will still cost a lot of dough.Plus the purchase of the catamaran.

Just realize that if you buy real estate with a heloc, be careful as now you are basically leveraging existing assets for new assets and many times people get over levered and in trouble in those scenarios.