That's the "if you've lived in it for two of the last five years you can exclude $250K (single) or $500K (married filing joint) from capital gains tax" rule. 

@Mary Ann CaseyYou could put it all under 1 Umbrella Policy, but I think you would be violating the IRA rules with commingling your personal finances with your IRA...but I am no IRA expert.The maximum # of Umbrella policies would be 2.  1 covering all of the assets in the IRA Second going over your personal home and auto, along with all of the rentals.

Hi @Jason Moran, @Dmitriy Fomichenko may be able to help.A couple other items to keep in mind: these conversions typically take weeks and you should factor that into your contract and, if you haven't already done so, familiarize your self with the rules and impacts of using leverage in combination with your IRA.

However, if you're torn between 2 great options with one being familiar and one not, the familiar one breaks the tie IMO.If you're looking to use the property as a short-term rental, the following locations rank as the 5 best places to buy in 2018 (according to a recent report): Panama City Beach, FloridaChicago, IllinoisNapa, CaliforniaTulsa, OklahomaMemphis, TennesseeYou'll also want to consider any additional costs that may be required to effectively run the rental depending on the location and condition the property is in when it's purchased; including home upgrades, management fees, taxes, insurance, and utilities.Before you get in too deep, though, you'll want to check in on the local policies, rules, and regulations to ensure all of your bases are covered.

Lessons Learned:I know I will hit this hurdle. 90 day FHA rule.

As Wayne and Harjeet said, if you do have an FHA loan outstanding and are forced to move, you would be exempt from the rule and allowed to obtain an additional FHA loan. 

They probably prefer having residents paying HOA dues.What are the "rules" for these HOA owned homes?

All the rules and responsibilities should be very explicitly listed in the operating agreement.

There's been a lot of attention recently on a few landlords who were gaming the system and the City's aldermen are cracking down on abuses, but I think that those landlords are more the exception than the rule. 

@Sophie Lavet These types of rules vary by state so you will want to check your local laws to be sure.