@Lee Banks I learned by reading.

I second a lot of what has been stated by others in this forum.

Originally posted by @Danny Johnson:@Luke Grogan I'd love to talk strategy with you regarding the systems you've been looking at. 

Regardless of your approach, forming an LLC is the smartest choice for protecting yourself from potential liability caused by the numerous tenants you will be hosting in your property.

@Tobi Isaacs this would be better answered by other investors in your market. 

They are known as the Winthrop Factors-The purpose for which the property was initially acquiredThe purpose for which the property was subsequently heldThe extent of improvements made to the propertyThe number and frequency of sales over timeThe extent to which the property has been disposed ofThe nature of the taxpayer’s business, including other activities and assetsThe amount of advertising/promotion, either directly or through a third partyThe listing of the property for sale through a brokerThe purpose of the held property at time of sale; the classification as an investor or dealer is determined on a property-by-property basis.To me intentionally buying a property to renovate it to resell it for profit, twice in the same year, and opened an entity to do it in ....is going to be ordinary income and not capital gains. 

And yep, in F'ville or very close by. 

I got started in real estate investing by house hacking myself as well!

Can you count purchases made by friends/family as expenses?

This a was a deteriorated house on my street that was previously occupied by a drug dealer.