STR demand is there, but regulations can be stricter.2.

It'll likely pick up again at some point, I'm hoping that this summer will be much better than last year was. 

Excited to hear more about your thoughts on what you think would be an initial plan.

That being said, you can do a lot bigger deals when employing others' money.

I am not able to take equity out of my condo because it is currently on the blacklist due to HOA fixing the roofing and a Fannie Mae rule stating, if more then 50% of the condos in that community are owned by investors, I may not be able to refi.

It's also new construction and everything will be under warranty for a while.

This would be via STR loophole, not REP status. 

@Wynn Williams You could buy it subject to the existing mortgage, but I'm hearing about those due-on-sale clauses being exercised often now.I would structure it as a lease with an option to buy.

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. 

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